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Vitamin A Acetate

Vitamin A Acetate

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Also known as: Vitamin a acetate, Retinol acetate, 127-47-9, Retinol, acetate, All-trans-retinyl acetate, Crystalets

Molecular Formula

C₂₂H₃₂O₂

Molecular Weight

328.5 g/mol

InChI Key

QGNJRVVDBSJHIZ-QHLGVNSISA-N

FDA UNII

3LE3D9D6OY

Retinyl Acetate is a naturally-occurring fatty acid ester form of retinol (vitamin A) with potential antineoplastic and chemopreventive activities. Retinyl acetate binds to and activates retinoid receptors, inducing cell differentiation and decreasing cell proliferation. This agent also inhibits carcinogen-induced neoplastic transformation in some cancer cell types and exhibits immunomodulatory properties. (NCI04)

1 2D Structure

Vitamin A Acetate

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-tetraenyl] acetate

2.1.2 InChI

InChI=1S/C22H32O2/c1-17(9-7-10-18(2)14-16-24-20(4)23)12-13-21-19(3)11-8-15-22(21,5)6/h7,9-10,12-14H,8,11,15-16H2,1-6H3/b10-7+,13-12+,17-9+,18-14+

2.1.3 InChI Key

QGNJRVVDBSJHIZ-QHLGVNSISA-N

2.1.4 Canonical SMILES

CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CCOC(=O)C)C)C

2.1.5 Isomeric SMILES

CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/COC(=O)C)/C)/C

2.2 Other Identifiers

2.2.1 UNII

3LE3D9D6OY

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 9-cis-retinyl Acetate

2. All-trans-retinyl Acetate

3. Dagravit A Forte

4. Dif Vitamin A Masivo

5. Qlt091001

6. Retinit

7. Retinol Acetate

8. Retinol Acetate, (9,13-cis)-isomer

9. Vitamin A Acetate

10. Vitamin A Dispersa

11. Vitamin-a-saar

2.3.2 Depositor-Supplied Synonyms

1. Vitamin A Acetate

2. Retinol Acetate

3. 127-47-9

4. Retinol, Acetate

5. All-trans-retinyl Acetate

6. Crystalets

7. Vitamin A1 Acetate

8. All-trans-retinol Acetate

9. Vitamin A Alcohol Acetate

10. Davitan A 650

11. Vitamin A Ester

12. All-trans-vitamin A Acetate

13. Retinol, Acetate, All-trans-

14. O~15~-acetylretinol

15. Nsc 122045

16. Trans-retinyl Acetate

17. [(2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] Acetate

18. Ro 1-5275

19. Retinol Acetate [jan]

20. Trans-vitamin A Acetate

21. Myvak (van)

22. Myvax (van)

23. 3le3d9d6oy

24. All-trans-retinylacetate

25. (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl Acetate

26. Chebi:32095

27. Vitamin A Acetate (van)

28. Acetic Acid, Retinyl Ester

29. Nsc-122045

30. Nsc-122760

31. Ncgc00090756-09

32. Retinol Acetate/all-trans-retinyl Acetate

33. Dsstox_cid_1240

34. Dsstox_rid_76032

35. Dsstox_gsid_21240

36. Vitaminaacetate

37. Vitamin A Acetate (tritiated)

38. Vitamin A, Acetate

39. Retinol, Acetate, Labeled With Tritium

40. O(15)-acetylretinol

41. 9-cis Retinol Acetate

42. Retinyl Acetate, All-trans-

43. Cas-127-47-9

44. Ccris 1907

45. Trans-retinol Acetate

46. Sr-05000001431

47. Einecs 204-844-2

48. Unii-3le3d9d6oy

49. Brn 1915439

50. Retinyl-acetate

51. Wln: L6utj A1 B1u1y1 & U2u1y1 & U2ov1 C1 C1

52. Vitamin A Acetat

53. 34356-31-5

54. Acetic Acid Retinyl

55. Mfcd00019413

56. Oristar Ra

57. (13z)-retinol Acetate

58. Spectrum5_001195

59. Spectrum5_002001

60. Retinol Acetate (jp17)

61. Retinyl (retinol) Acetate

62. Ec 204-844-2

63. Retinol, O~15~-acetyl-

64. Bspbio_002833

65. Spectrum1503051

66. Retinyl Acetate [inci]

67. C22h32o2 (retinol Acetate)

68. Chembl486193

69. Vitamin A Acetate [mi]

70. Dtxsid6021240

71. Chebi:94695

72. Hms501k04

73. Retinol Acetate [who-dd]

74. Retinyl Acetate [usp-rs]

75. Vitamin A Acetate [vandf]

76. Hms1922a19

77. Hms2089g20

78. Pharmakon1600-01503051

79. Amy13865

80. Hy-n0679

81. Zinc3874857

82. Retinyl Acetate, Analytical Standard

83. Tox21_113549

84. Tox21_201423

85. Tox21_302737

86. Bdbm50442911

87. Ccg-39564

88. Lmpr01090012

89. Nsc122045

90. Nsc122760

91. Nsc758220

92. S4083

93. Akos015914999

94. Tox21_113549_1

95. Cs-8187

96. Nsc-758220

97. Idi1_000522

98. Ncgc00090756-01

99. Ncgc00090756-02

100. Ncgc00090756-03

101. Ncgc00090756-05

102. Ncgc00090756-06

103. Ncgc00090756-07

104. Ncgc00090756-08

105. Ncgc00090756-10

106. Ncgc00090756-11

107. Ncgc00090756-12

108. Ncgc00256509-01

109. Ncgc00258974-01

110. Vitamin A (as Acetate) [vandf]

111. 64536-04-5

112. Ac-19999

113. All-(e)-retinol Acetate [who-ip]

114. Sbi-0051756.p002

115. Vitamin A Acetate 1.5 M.i.u./g

116. Ro-1-5275

117. A16783

118. D01621

119. H12041

120. Vitamin A Acetate 10 Microg/ml In Acetonitrile

121. Ab00052305-02

122. Ab00052305_03

123. Vitamin A Acetate In Gelatin, 500,000 I.u./g

124. Q7316808

125. Sr-05000001431-1

126. Sr-05000001431-3

127. W-108382

128. Brd-k65331431-001-01-3

129. Vitamin A (acetate), Meets Usp Testing Specifications

130. Vitamin A (as Acetate & Beta Carotene) [vandf]

131. Retinol Acetate, European Pharmacopoeia (ep) Reference Standard

132. Retinyl Acetate, Synthetic, Crystalline Solid Or Supercooled Liquid

133. Retinyl Acetate, United States Pharmacopeia (usp) Reference Standard

134. Retinyl Acetate, Concentrate (~50% (w/w) In Peanut Oil), ~1500 U/mg

135. Retinyl Acetate, Solid Or Viscous Liquid, Bioreagent, Synthetic, Suitable For Cell Culture

136. Retinyl Acetate, Synthetic, Matrix Dispersion, 475,000-650,000 Usp Units/g

137. (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenyl Acetate

138. 3,7-dimethyl-9-(2,6,6,-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol Acetate, (all Trans)-

139. Retinyl Acetate (vitamin A Acetate), Pharmaceutical Secondary Standard; Certified Reference Material

140. Retinyl Acetate Solution, 100 Mug/ml In Ethanol (with 0.1% (w/v) Bht), Ampule Of 1 Ml, Certified Reference Material

141. Retinyl Acetate Solution, 100 Mug/ml In Ethanol (with 0.1% (w/v) Bht; Degassed), Certified Reference Material

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₃₂O₂
Molecular Weight	328.5 g/mol
XLogP3	6.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	7
Exact Mass	328.240230259 g/mol
Monoisotopic Mass	328.240230259 g/mol
Topological Polar Surface Area	26.3 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	596
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	4
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anticarcinogenic Agents

Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved. (See all compounds classified as Anticarcinogenic Agents.)

Adjuvants, Immunologic

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)

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