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Chemistry

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Also known as: Vitamin a, All-trans-retinol, 68-26-8, Vitamin a1, Alphalin, Axerophthol
Molecular Formula
C20H30O
Molecular Weight
286.5  g/mol
InChI Key
FPIPGXGPPPQFEQ-OVSJKPMPSA-N
FDA UNII
G2SH0XKK91

Vitamin A
Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.
1 2D Structure

Vitamin A

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol
2.1.2 InChI
InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
2.1.3 InChI Key
FPIPGXGPPPQFEQ-OVSJKPMPSA-N
2.1.4 Canonical SMILES
CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CCO)C)C
2.1.5 Isomeric SMILES
CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/CO)/C)/C
2.2 Other Identifiers
2.2.1 UNII
G2SH0XKK91
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 11-cis-retinol

2. 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-e)-isomer

3. All Trans Retinol

4. All-trans-retinol

5. Aquasol A

6. Vitamin A

7. Vitamin A1

2.3.2 Depositor-Supplied Synonyms

1. Vitamin A

2. All-trans-retinol

3. 68-26-8

4. Vitamin A1

5. Alphalin

6. Axerophthol

7. Afaxin

8. Vitamin A Alcohol

9. Oleovitamin A

10. Chocola A

11. Alphasterol

12. Apostavit

13. Aquasynth

14. Biosterol

15. Epiteliol

16. Ophthalamin

17. Agiolan

18. Agoncal

19. Anatola

20. Myvpack

21. Prepalin

22. Testavol

23. Veroftal

24. Aoral

25. Apexol

26. Avibon

27. Avitol

28. Axerol

29. Dofsol

30. Trans-retinol

31. Vaflol

32. Vitpex

33. Vogan

34. Disatabs Tabs

35. Lard Factor

36. All-trans-retinyl Alcohol

37. Bentavit A

38. Dohyfral A

39. Alcovit A

40. Anatola A

41. Vogan-neu

42. A-mulsal

43. Plivit A

44. Vi-alpha

45. A-vitan

46. All-trans Retinol

47. Atars

48. Vafol

49. All-trans-vitamin A Alcohol

50. Retrovitamin A

51. Homagenets Aoral

52. A-sol

53. Hi-a-vita

54. Sehkraft A

55. Vitamin A1 Alcohol

56. All-trans-vitamin A

57. A-vi-pel

58. Acon

59. Atav

60. Vi-dom-a

61. 11103-57-4

62. Super A

63. Anti-infective Vitamin

64. Solu-a

65. Nio-a-let

66. Vio-a

67. Antixerophthalmic Vitamin

68. Del-vi-a

69. Vitavel A

70. Thalasphere

71. Beta-retinol

72. Trans-vitamin A Alcohol

73. Vitamin A Alcohol, All-trans-

74. Vitamin A1, All-trans-

75. Retinol, All Trans-

76. All-trans-vitamin A1

77. Vitamin A Oil

78. .beta.-retinol

79. (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol

80. (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol

81. Vitamin A1 Alcohol, All-trans-

82. (all-e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol

83. Chembl986

84. Nsc-122759

85. G2sh0xkk91

86. 2,4,6,8-nonatetraen-1-ol, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-e)-

87. Axerophtholum

88. Chebi:17336

89. Wachstumsvitamin

90. All-trans-13,14-dihydro Retinol

91. Vitaminum A

92. Vitamine A

93. Vitavel-a

94. Vitamina

95. Retinolo [dcit]

96. Ncgc00017343-07

97. Cylasphere

98. Retinolo

99. Retinolum

100. Retinol [inn:ban]

101. Dsstox_cid_3556

102. Hydrovit A

103. Retinolum [inn-latin]

104. 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol

105. Dsstox_rid_77080

106. Dsstox_gsid_23556

107. Ro-a-vit

108. Trol

109. Vitamin A Alcohol (van)

110. Antixerophthalmisches Vitamin

111. Aquasol A Parenteral

112. Vi-alpha; Vi-alpha

113. Rovimix A 500

114. 9-cis Retinol

115. Vitamin A1 Alcohol, All Trans

116. Retinol Solution

117. Cas-68-26-8

118. Smr000112036

119. Retinol (vit A)

120. [11,12-3h]-retinol

121. 9-cis,13-cis-retinol

122. Vitamin A (usp)

123. Ccris 5444

124. Hsdb 815

125. Vitamin A [natural]

126. Sr-01000763813

127. Retin-11,12-t2-ol (9ci)

128. Einecs 200-683-7

129. Mfcd00001552

130. Unii-g2sh0xkk91

131. Nsc 122759

132. Brn 0403040

133. Unii-81g40h8b0t

134. Tegosphere Vita

135. .alpha.sterol

136. B-retinol

137. .alpha.lin

138. Retinyl A

139. Trans-retinol Acid (vitamin A)

140. 1rbp

141. Vi-.alpha.

142. Einecs 234-328-2

143. 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclchexen-1-yl)-2,4,6,8-nonatetraen-1-ol

144. (9z)-retinol

145. 1gx8

146. Retinol-(cellular-retinol-binding-protein)

147. Retinol [hsdb]

148. Retinol [inci]

149. Retinol [inn]

150. Spectrum5_000993

151. Spectrum5_001997

152. Vitamin A [mi]

153. Retinol [who-dd]

154. Retinol, 95%, Synthetic

155. Ec 200-683-7

156. All-trans Vitamin A Alcohol

157. Schembl3112

158. 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonate-traen-1-ol

159. 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-e)-

160. Alcohol 9,13-dimethyl-7-(1,1,5-trimethyl-6-cyclohexen-5-yl)-7,9,11,13-nonatetraen-15-ol

161. Bidd:pxr0102

162. 4-06-00-04133 (beilstein Handbook Reference)

163. Mls001066379

164. Mls001074751

165. Mls006010008

166. Retinol, All-trans- (8ci)

167. Spectrum1501203

168. Gtpl4053

169. Dtxsid3023556

170. Hms501i08

171. 81g40h8b0t

172. Hms1921b04

173. Hms2092l13

174. Hms2270c05

175. Pharmakon1600-01501203

176. Bcp06593

177. Hy-b1342

178. Zinc3831417

179. Tox21_110818

180. Tox21_202441

181. Tox21_300287

182. Bdbm50092056

183. Ccg-38864

184. Lmpr01090001

185. Nsc122759

186. Nsc758150

187. S5592

188. Akos015902578

189. Db00162

190. Nsc-758150

191. Sdccgmls-0066724.p001

192. (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetr Aen-1-ol

193. Idi1_000486

194. Retinol Solution, >=95.0% (hplc)

195. Smp2_000102

196. Ncgc00017343-02

197. Ncgc00017343-03

198. Ncgc00017343-04

199. Ncgc00017343-05

200. Ncgc00017343-06

201. Ncgc00017343-08

202. Ncgc00017343-09

203. Ncgc00017343-11

204. Ncgc00091784-01

205. Ncgc00091784-02

206. Ncgc00091784-03

207. Ncgc00091784-04

208. Ncgc00091784-05

209. Ncgc00091784-06

210. Ncgc00254024-01

211. Ncgc00259990-01

212. Ac-11701

213. Bs-17906

214. Sbi-0051690.p002

215. Cs-0013091

216. C00473

217. C17276

218. D06543

219. Ab00052248_05

220. 103v574

221. A836068

222. Q424976

223. Retinol, >=95.0% (hplc), ~2700 U/mg

224. Retinol, Synthetic, >=95% (hplc), Crystalline

225. J-014834

226. J-017515

227. Q-201926

228. Sr-01000763813-2

229. Sr-01000763813-4

230. W-104683

231. Brd-k22429181-001-06-8

232. Brd-k64634304-001-01-5

233. Wln: L6utj A1 B1u1y1&u2u1y1&u2q C1 C1

234. Retinol, Bioxtra, >=97.5% (hplc), ~3100 U/mg

235. 3,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol

236. 2,6,8-nonatetraen-1-ol, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-e)-

237. 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, All (e)-

238. (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-1-nona-2,4,6,8-tetraenol

239. (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraen-1-ol

240. (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraen-1-ol

241. (2z,4z,6z,8z)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetren-1-ol

242. Retinol Solution, 100 Mug/ml +/- 25% (refer To Coa) (ethanol With 0.1% (w/v) Bht), Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 286.5 g/mol
Molecular Formula C20H30O
XLogP35.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count5
Exact Mass286.229665576 g/mol
Monoisotopic Mass286.229665576 g/mol
Topological Polar Surface Area20.2 Ų
Heavy Atom Count21
Formal Charge0
Complexity496
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count4
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Vitamin A is indicated only for prevention or treatment of vitamin A deficiency states. Vitamin A deficiency may occur as a result of inadequate nutrition or intestinal malabsorption but does not occur in healthy individual receiving an adequate balanced diet. For prophylaxis of vitamin A deficiency, dietary improvement, rather than supplementation, is advisable. For treatment of vitamin A deficiency, supplementation is preferred. /Included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2841


Recommended intakes may be increased and/or supplementation may be necessary in infants receiving unfortified formula or in individuals with the following conditions (based on documented vitamin A deficiency): Diarrhea; gastrectomy; hyperthyroidism; infections, chronic; intestinal diseases: celiac, diarrhea, topical sprue, regional enteritis; malabsorption syndromes associated with pancreatic insufficiency: pancreatic disease, cystic fibrosis; measles; protein deficiency, severe, stress, prolonged; xerophthalmia. /Included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2841


Some unusual diets (e.g., reducing diets that drastically restrict food selection, especially the fat-containing foods) may not supply minimum daily recommended intakes of vitamin A. Supplementation is necessary in patients receiving total parenteral nutrition (TPN) or undergoing rapid weight loss or in those with malnutrition, because of inadequate dietary intake.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2841


Recommended intakes for most vitamins and minerals are increased during pregnancy. Many physicians recommend that pregnant women receive multivitamin and mineral supplements, especially those pregnant women who do not consume an adequate diet and those in high-risk categories (i.e., women carrying more than one fetus, heavy cigarette smokers, and alcohol and drug abusers). Taking excessive amounts of a multivitamin and mineral supplement may be harmful to the mother and/or fetus and should be avoided.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2841


For more Therapeutic Uses (Complete) data for VITAMIN A (7 total), please visit the HSDB record page.


4.2 Drug Warning

Pregnancy risk category: X /CONTRAINDICATED IN PREGNANCY. Studies in animals or humans, or investigational or post-marketing reports, have demonstrated positive evidence of fetal abnormalities or risk which clearly outweights any possible benefit to the patient./ /Parenteral vitamin A/

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2842


Doses of vitamin A that do not exceed the physiologic requirement are usually nontoxic.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 3490


There are insufficient data to show that vitamin A may reduce the occurrence of certain types of cancer.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2841


... Vitamin A has not been proven effective for treatment of renal calculi, hyperthyroidism, anemia, degenerative conditions of the nervous system, sunburn, lung diseases, deafness, osteoarthritis, inflammatory bowel disease, or psoriasis.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2841


For more Drug Warnings (Complete) data for VITAMIN A (9 total), please visit the HSDB record page.


4.3 Drug Indication

For the treatment of vitamin A deficiency.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Vitamin A is effective for the treatment of Vitamin A deficiency. Vitamin A refers to a group of fat-soluble substances that are structurally related to and possess the biological activity of the parent substance of the group called all-trans retinol or retinol. Vitamin A plays vital roles in vision, epithelial differentiation, growth, reproduction, pattern formation during embryogenesis, bone development, hematopoiesis and brain development. It is also important for the maintenance of the proper functioning of the immune system.


5.2 MeSH Pharmacological Classification

Vitamins

Organic substances that are required in small amounts for maintenance and growth, but which cannot be manufactured by the human body. (See all compounds classified as Vitamins.)


5.3 FDA Pharmacological Classification
5.3.1 Pharmacological Classes
Vitamin A [EPC]; Vitamin A [CS]
5.4 ATC Code

A - Alimentary tract and metabolism

A11 - Vitamins

A11C - Vitamin a and d, incl. combinations of the two

A11CA - Vitamin a, plain

A11CA01 - Retinol (vit A)


D - Dermatologicals

D10 - Anti-acne preparations

D10A - Anti-acne preparations for topical use

D10AD - Retinoids for topical use in acne

D10AD02 - Retinol


R - Respiratory system

R01 - Nasal preparations

R01A - Decongestants and other nasal preparations for topical use

R01AX - Other nasal preparations

R01AX02 - Retinol


S - Sensory organs

S01 - Ophthalmologicals

S01X - Other ophthalmologicals

S01XA - Other ophthalmologicals

S01XA02 - Retinol


5.5 Absorption, Distribution and Excretion

Absorption

Readily absorbed from the normal gastrointestinal tract


Vitamin A is distributed into breast milk ... .

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2842


Less than 5% of circulating vitamin A is bound to lipoproteins in blood (normal), but may be up to 65% when hepatic stores are saturated because of excessive intake. The amount of vitamin A bound to lipoproteins may be increased in hyperlipoproteinemia. When released from liver, vitamin A is bound to retinol-binding protein (RBP). Most vitamin A circulates in the form of retinol bound to RBP.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2841


Storage: Hepatic (approximately 2 years' adult requirements), with small amounts stored in kidney and lung tissues. Zinc is required for mobilization of vitamin A reserves in the liver.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2841


More than 90% of the intake of preformed vitamin A is in the form of retinol esters, usually as retinyl palmitate. ... When a large excess is ingested, some of the vitamin escapes in the feces. ... Absorption ... is related to that of lipid and is enhanced by bile. ... Aqueous dispersions ... are absorbed more rapidly than are oily solution.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1779


For more Absorption, Distribution and Excretion (Complete) data for VITAMIN A (9 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Hepatic. Retinol is conjugated with glucuronic acid; the B-glucuronide undergoes enterohepatic circulation and oxidation to retinol and retinoic acid. Retinoic acid undergoes decarboxylation and conjugation with glucuronic acid.


Retinol is converted to retinyl phosphate in epithelial tissues, and this intermediate is in turn metabolized to mannosylretinylphosphate in a reaction that is catalyzed by a microsomal enzyme and requires guanosine diphosphomannose as a glycosyl donor. ... /the vitamin A/ mediates transfer of mannose to specific glycoproteins.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1777


Retinol is in part conjugated to form a beta-glucuronide, which undergoes enterohepatic circulation and is oxidized to retinal and retinoic acid.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1781


Within the retina, all-trans-retinol is oxidized to retinal by alcohol dehydrogenases, and is then Isomerized to the 11-cis-isomer which combines with opsin in the rod to yield rhodopsin, and with different opsins in human cones to yield three different iodopsin pigments.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 254


Retinoic acid (RA) is the bioactive metabolite of vitamin A (retinol) which acts on cells to establish or change the pattern of gene activity. Retinol is converted to RA by the action of two types of enzyme, retinol dehydrogenases and retinal dehydrogenases. In the nucleus RA acts as a ligand to activate two families of transcription factors, the RA receptors (RAR) and the retinoid X receptors (RXR) which heterodimerize and bind to the upstream sequences of RA-responsive genes.

PMID:10828175 Maden M; Proc Nutr Soc 59 (1): 65-73 (2000)


Retinol has known human metabolites that include 4-Hydroxyretinol and retinal.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.7 Biological Half-Life

1.9 hours


Hepatic reserves of vitamin A decrease with a half-life of about 50 days in animals ...

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1589


5.8 Mechanism of Action

Vision:Vitamin A (all-trans retinol) is converted in the retina to the 11-cis-isomer of retinaldehyde or 11-cis-retinal. 11-cis-retinal functions in the retina in the transduction of light into the neural signals necessary for vision. 11-cis-retinal, while attached to opsin in rhodopsin is isomerized to all-trans-retinal by light. This is the event that triggers the nerve impulse to the brain which allows for the perception of light. All-trans-retinal is then released from opsin and reduced to all-trans-retinol. All-trans-retinol is isomerized to 11-cis-retinol in the dark, and then oxidized to 11-cis-retinal. 11-cis-retinal recombines with opsin to re-form rhodopsin. Night blindness or defective vision at low illumination results from a failure to re-synthesize 11-cis retinal rapidly.
Epithelial differentiation: The role of Vitamin A in epithelial differentiation, as well as in other physiological processes, involves the binding of Vitamin A to two families of nuclear retinoid receptors (retinoic acid receptors, RARs; and retinoid-X receptors, RXRs). These receptors function as ligand-activated transcription factors that modulate gene transcription. When there is not enough Vitamin A to bind these receptors, natural cell differentiation and growth are interrupted.


Topical vitamin A can reverse the impairment of wound healing seen in patients receiving corticosteroids, perhaps by restoring the normal inflammatory reaction in the wound. The possibility has been suggested that systemic vitamin A could inhibit the anti-inflammatory effect of systemic corticosteroids.

Hansten P.D. Drug Interactions. 5th ed. Philadelphia: Lea and Febiger, 1985., p. 322


Retinol arrested proliferation of cultured neuroblastoma cells at concentrations of 50 um. A correlation existed between inhibition of growth and inhibition of ornithine decarboxylase in both neuroblastoma cells and glioma cells with retinol.

PMID:6770209 Chapman S; LIFE SCI 26 (16): 1359 (1980)


In rats exptl-hypervitaminosis A has been shown ... to produce severe damage of the retina, mainly in the pigment epithelium according to electron microscopy. Alcohol dehydrogenase activity was shown to disappear in the pigment epithelium and visual cells ... .

Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 9795


/The authors/ have shown that in an experimental cell culture system consisting of carcinogen-treated 10T1/2 cells, both retinoids and all dietary carotenoids examined can reversibly inhibit neoplastic transformation in the post-initiation phase of carcinogenesis. This activity strongly correlates with their ability to increase gap junctional intercellular communication by up-regulating the expression of the gene CX43 (connexin43). Connexins comprise the structural unit of gap junctions, organelles which allow direct transfer of signals, nutrients and waste products between contacting cells. CX43 is the most widely expressed member of the gap junction family of genes, and we have demonstrated that its expression is strongly down-regulated in human cancers and in several premalignant conditions. When several human tumour cell lines were genetically engineered to conditionally express CX43 under the influence of a tetracycline promoter, their neoplastic phenotype was strongly attenuated. Specifically, induced cells were inhibited from growing in an anchorage-independent manner and, additionally, growth as xenografts in immunocompromised animals was also strongly attenuated. Growth inhibition in suspension was associated both with increased G(1) cell-cycle arrest and with increased apoptosis. /The authors/ propose a model whereby junctional communication allows the transfer of growth inhibitory signals from normal to neoplastic cells and that retinoids and carotenoids, by increasing signal transfer, act to prevent cancer.

PMID:15506943 Bertram JS; Biochem Soc Trans 32 (Pt 6) :985-9 (2004)


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MAHARASHTRA.","supplier":"DSM NUTRITIONAL PRODUCTS ASIA PACIFIC","supplierCountry":"SWITZERLAND","foreign_port":"ANTWERPEN","customer":"DSM NUTRITIONAL PRODUCTS INDIA PRIVATE LTD","customerCountry":"INDIA","quantity":"800.00","actualQuantity":"800","unit":"KGS","unitRateFc":"61.4","totalValueFC":"49316.7","currency":"INR","unitRateINR":"5252.3","date":"09-May-2025","totalValueINR":"4201816","totalValueInUsd":"49316.7","indian_port":"JNPT","hs_no":"29362100","bill_no":"9952090","productDescription":"API","marketType":"REGULATED MARKET","country":"SWITZERLAND","selfForZScoreResived":"Pharma Grade","supplierPort":"ANTWERPEN","supplierAddress":"30 PASIR PANJANG ROAD #13-31, MAPLE TREE BUSINESS CITY, Singapore - 117 440, , Singapore Singapore","customerAddress":"401 4TH FL WINDSOR HOUSE CST RD"},{"dataSource":"API Import","activeIngredients":"","year":"2025","qtr":"Q2","strtotime":1747593000,"product":"DRY VITAMIN A PALMITATE 250 S\/N - FRANCE DRY VITAMIN A PALMITATE 250 S\/N - FRANCE","address":"401 4TH FL WINDSOR HOUSE CST RD","city":"MUMBAI, MAHARASHTRA.","supplier":"DSM NUTRITIONAL PRODUCTS ASIA PACIFIC","supplierCountry":"FRANCE","foreign_port":"ROTTERDAM","customer":"DSM NUTRITIONAL PRODUCTS INDIA PRIVATE LTD","customerCountry":"INDIA","quantity":"900.00","actualQuantity":"900","unit":"KGS","unitRateFc":"18.5","totalValueFC":"16914.5","currency":"USD","unitRateINR":"1601.3","date":"19-May-2025","totalValueINR":"1441125","totalValueInUsd":"16914.5","indian_port":"JNPT","hs_no":"29362100","bill_no":"2137199","productDescription":"API","marketType":"REGULATED MARKET","country":"FRANCE","selfForZScoreResived":"Pharma Grade","supplierPort":"ROTTERDAM","supplierAddress":"30 PASIR PANJANG ROAD #13-31, MAPLE TREE BUSINESS CITY, Singapore - 117 440, , Singapore Singapore","customerAddress":"401 4TH FL WINDSOR HOUSE CST RD"},{"dataSource":"API Import","activeIngredients":"","year":"2025","qtr":"Q2","strtotime":1748457000,"product":"DRY VITAMIN A ACETATE 325 CWS\/A - SWITZERLAND DRY VITAMIN A ACETATE 325 CWS\/A - SWITZERLAND","address":"401 4TH FL WINDSOR HOUSE CST RD","city":"MUMBAI, MAHARASHTRA.","supplier":"DSM NUTRITIONAL PRODUCTS ASIA PACIFIC","supplierCountry":"SWITZERLAND","foreign_port":"ROTTERDAM","customer":"DSM NUTRITIONAL PRODUCTS INDIA PRIVATE LTD","customerCountry":"INDIA","quantity":"450.00","actualQuantity":"450","unit":"KGS","unitRateFc":"53.3","totalValueFC":"24338.5","currency":"USD","unitRateINR":"4608.1","date":"29-May-2025","totalValueINR":"2073658.5","totalValueInUsd":"24338.5","indian_port":"JNPT","hs_no":"29362100","bill_no":"2339965","productDescription":"API","marketType":"REGULATED MARKET","country":"SWITZERLAND","selfForZScoreResived":"Pharma Grade","supplierPort":"ROTTERDAM","supplierAddress":"30 PASIR PANJANG ROAD #13-31, MAPLE TREE BUSINESS CITY, Singapore - 117 440, , Singapore Singapore","customerAddress":"401 4TH FL WINDSOR HOUSE CST RD"}]
04-Jan-2022
29-May-2025
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DRUG PRODUCT COMPOSITIONS

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DOSAGE - FOR SOLUTION;INTRAVENOUS - 80MG/VIAL...DOSAGE - FOR SOLUTION;INTRAVENOUS - 80MG/VIAL;0.02MG/VIAL;0.001MG/VIAL;5MG/VIAL;0.01MG/VIAL;0.14MG/VIAL;17MG/VIAL;0.2MG/VIAL;1MG/VIAL;1.4MG/VIAL;EQ 1.2MG BASE/VIAL;0.7MG/VIAL;7MG/VIAL

USFDA APPLICATION NUMBER - 18920

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DOSAGE - INJECTABLE;INTRAVENOUS - 200MG/VIAL;...DOSAGE - INJECTABLE;INTRAVENOUS - 200MG/VIAL;0.06MG/VIAL;0.005MG/VIAL;15MG/VIAL;0.005MG/VIAL;0.6MG/VIAL;40MG/VIAL;6MG/VIAL;3.6MG/VIAL;6MG/VIAL;1MG/VIAL;10MG/VIAL;0.15MG/VIAL

USFDA APPLICATION NUMBER - 21625

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DOSAGE - INJECTABLE;INJECTION - 20MG/ML;0.006...DOSAGE - INJECTABLE;INJECTION - 20MG/ML;0.006MG/ML;0.05MCG/ML;1.5MG/ML;0.0005MG/ML;0.06MG/ML;4MG/ML;0.6MG/ML;0.36MG/ML;0.6MG/ML;0.1MG/ML;1MG/ML

USFDA APPLICATION NUMBER - 8809

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ABOUT THIS PAGE

Looking for 68-26-8 / Vitamin A API manufacturers, exporters & distributors?

Vitamin A manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Vitamin A API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Vitamin A manufacturer or Vitamin A supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Vitamin A manufacturer or Vitamin A supplier.

PharmaCompass also assists you with knowing the Vitamin A API Price utilized in the formulation of products. Vitamin A API Price is not always fixed or binding as the Vitamin A Price is obtained through a variety of data sources. The Vitamin A Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Vitamin A

Synonyms

All-trans-retinol, 68-26-8, Vitamin a1, Alphalin, Axerophthol, Afaxin

Cas Number

68-26-8

Unique Ingredient Identifier (UNII)

G2SH0XKK91

About Vitamin A

Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of CAROTENOIDS found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products.

VITAMINA Manufacturers

A VITAMINA manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of VITAMINA, including repackagers and relabelers. The FDA regulates VITAMINA manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. VITAMINA API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of VITAMINA manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

VITAMINA Suppliers

A VITAMINA supplier is an individual or a company that provides VITAMINA active pharmaceutical ingredient (API) or VITAMINA finished formulations upon request. The VITAMINA suppliers may include VITAMINA API manufacturers, exporters, distributors and traders.

click here to find a list of VITAMINA suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

VITAMINA USDMF

A VITAMINA DMF (Drug Master File) is a document detailing the whole manufacturing process of VITAMINA active pharmaceutical ingredient (API) in detail. Different forms of VITAMINA DMFs exist exist since differing nations have different regulations, such as VITAMINA USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A VITAMINA DMF submitted to regulatory agencies in the US is known as a USDMF. VITAMINA USDMF includes data on VITAMINA's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The VITAMINA USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of VITAMINA suppliers with USDMF on PharmaCompass.

VITAMINA JDMF

The Pharmaceuticals and Medical Devices Agency (PMDA) established the Japan Drug Master File (JDMF), also known as the Master File (MF), to permit Japanese and foreign manufacturers of drug substances, intermediates, excipients, raw materials, and packaging materials (‘Products’) to voluntarily register confidential information about the production and management of their products in Japan.

The VITAMINA Drug Master File in Japan (VITAMINA JDMF) empowers VITAMINA API manufacturers to present comprehensive information (e.g., production methods, data, etc.) to the review authority, i.e., PMDA (Pharmaceuticals & Medical Devices Agency).

PMDA reviews the VITAMINA JDMF during the approval evaluation for pharmaceutical products. At the time of VITAMINA JDMF registration, PMDA checks if the format is accurate, if the necessary items have been included (application), and if data has been attached.

click here to find a list of VITAMINA suppliers with JDMF on PharmaCompass.

VITAMINA CEP

A VITAMINA CEP of the European Pharmacopoeia monograph is often referred to as a VITAMINA Certificate of Suitability (COS). The purpose of a VITAMINA CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of VITAMINA EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of VITAMINA to their clients by showing that a VITAMINA CEP has been issued for it. The manufacturer submits a VITAMINA CEP (COS) as part of the market authorization procedure, and it takes on the role of a VITAMINA CEP holder for the record. Additionally, the data presented in the VITAMINA CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the VITAMINA DMF.

A VITAMINA CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. VITAMINA CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

click here to find a list of VITAMINA suppliers with CEP (COS) on PharmaCompass.

VITAMINA GMP

VITAMINA Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of VITAMINA GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right VITAMINA GMP manufacturer or VITAMINA GMP API supplier for your needs.

VITAMINA CoA

A VITAMINA CoA (Certificate of Analysis) is a formal document that attests to VITAMINA's compliance with VITAMINA specifications and serves as a tool for batch-level quality control.

VITAMINA CoA mostly includes findings from lab analyses of a specific batch. For each VITAMINA CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

VITAMINA may be tested according to a variety of international standards, such as European Pharmacopoeia (VITAMINA EP), VITAMINA JP (Japanese Pharmacopeia) and the US Pharmacopoeia (VITAMINA USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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