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CAS 2216-51-5
Also known as: (-)-menthol, 2216-51-5, Levomenthol, L-(-)-menthol, Menthomenthol, Menthacamphor
Molecular Formula
C10H20O
Molecular Weight
156.26  g/mol
InChI Key
NOOLISFMXDJSKH-KXUCPTDWSA-N
FDA UNII
BZ1R15MTK7

Levomenthol is a levo isomer of menthol, an organic compound made synthetically or obtained from peppermint or mint oils with flavoring and local anesthetic properties. When added to pharmaceuticals and foods, menthol functions as a fortifier for peppermint flavors. It also has a counterirritant effect on skin and mucous membranes, thereby producing a local analgesic or anesthetic effect.
1 2D Structure

CAS 2216-51-5

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol
2.1.2 InChI
InChI=1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1
2.1.3 InChI Key
NOOLISFMXDJSKH-KXUCPTDWSA-N
2.1.4 Canonical SMILES
CC1CCC(C(C1)O)C(C)C
2.1.5 Isomeric SMILES
C[C@@H]1CC[C@H]([C@@H](C1)O)C(C)C
2.2 Other Identifiers
2.2.1 UNII
BZ1R15MTK7
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. (-)-menthol

2. 2216-51-5

3. Levomenthol

4. L-(-)-menthol

5. Menthomenthol

6. Menthacamphor

7. Peppermint Camphor

8. (1r,2s,5r)-2-isopropyl-5-methylcyclohexanol

9. U.s.p. Menthol

10. Levomentholum

11. Racementhol

12. (1r,2s,5r)-(-)-menthol

13. (-)-menthyl Alcohol

14. (-)-(1r,3r,4s)-menthol

15. Menthol Racemic

16. Hexahydrothymol

17. (1r)-(-)-menthol

18. D,l-menthol

19. (r)-(-)-menthol

20. 89-78-1

21. D-(-)-menthol

22. Menthol, Dl-

23. I-menthol

24. Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1r,2s,5r)-

25. P-menthan-3-ol

26. (-)-trans-p-menthan-cis-ol

27. Rac-menthol

28. 1-menthol

29. (l)-menthol

30. Menthol(-)

31. (1r,2s,5r)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol

32. Menthol, (1r,3r,4s)-(-)-

33. (1r,3r,4s)-(-)-menthol

34. Nci-c50000

35. Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1r,2s,5r)-rel-

36. 1r-menthol

37. Nsc 62788

38. Racemic Menthol

39. Water-soluble Menthol

40. (1r,2s,5r)-menthol

41. 5-methyl-2-(1-methylethyl)cyclohexanol

42. (1r,2s,5r)-2-isopropyl-5-methylcyclohexan-1-ol

43. (1r,2s,5r)-rel-2-isopropyl-5-methylcyclohexanol

44. Bz1r15mtk7

45. (1r,2s,5r)-5-methyl-2-(1-methylethyl)cyclohexanol

46. (1r-(1-alpha,2-beta,5-alpha))-5-methyl-2-(1-methylethyl)cyclohexanol

47. (1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexan-1-ol

48. Menthol Crystals

49. Chembl470670

50. Ys08xha860

51. Chebi:15409

52. Menthol Natural

53. Nsc2603

54. (1r,2s,5r)-2-isopropyl-5-methyl-cyclohexanol

55. (1r,2s,5s)-2-isopropyl-5-methyl-cyclohexanol

56. Headache Crystals

57. Nsc-2603

58. Fema No. 2665

59. Nsc-62788

60. Menthol (van)

61. Racementholum

62. Thymomenthol

63. Menthol, Cis-1,3,trans-1,4-

64. Racementol

65. L-menthol (natural)

66. Nsc 2603

67. (+-)-menthol

68. Dsstox_cid_2180

69. Menthol Racemique

70. Levomenthol [inn:ban]

71. Racementhol [inn:ban]

72. Cyclohexanol, 5-methyl-2-(1-methylethyl)-, [1r-(1.alpha.,2.beta.,5.alpha.)]-

73. Dsstox_rid_75798

74. Dsstox_rid_76516

75. Dsstox_gsid_20805

76. Dsstox_gsid_22180

77. Menthol Natural, Brazilian

78. Menthol, L-

79. Racementol [inn-spanish]

80. Rel-(1r,2s,5r)-2-isopropyl-5-methylcyclohexanol

81. Levomentholum [inn-latin]

82. Menthol Racemique [french]

83. Racementholum [inn-latin]

84. Tra-kill Tracheal Mite Killer

85. (1alpha,2beta,5alpha)-5-methyl-2(1-methylethyl)cyclohexanol

86. Mfcd00062979

87. Cas-89-78-1

88. Ccris 375

89. Cas-2216-51-5

90. L-menthol (tn)

91. Ccris 3728

92. Ccris 4666

93. Hsdb 5662

94. Sr-05000001936

95. (-)-p-menthan-3-ol

96. Einecs 201-939-0

97. Einecs 218-690-9

98. Einecs 239-388-3

99. Unii-bz1r15mtk7

100. Brn 1902288

101. Brn 3194263

102. Levomentol

103. Unii-ys08xha860

104. (+-)-(1r*,3r*,4s*)-menthol

105. Ss-bisabolol

106. Ai3-52408

107. Laevo-menthol

108. Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1.alpha.,2.beta.,5.alpha.)-

109. Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1r-(1alpha,2beta,5alpha))-

110. Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1r-(1.alpha.,2.beta.,5.alpha.))-

111. L-menthol Natural

112. 1 -menthol

113. Ncgc00159382-02

114. Dextro,laevo-menthol

115. Meggezone

116. Menthol Crystals Usp

117. L-mentholum

118. L-menthol (jp17)

119. Spectrum_000305

120. Levomenthol [ii]

121. Menthol [mi]

122. 5-methyl-2-(1-methylethyl)cyclohexanol, (1alpha,2beta,5alpha)-

123. L-menthol [jan]

124. Menthol, (+/-)-

125. Spectrum2_000855

126. Spectrum3_001561

127. Spectrum5_001060

128. Levomenthol [inn]

129. Racementhol [inn]

130. M0545

131. Dl-menthol [jan]

132. Menthol [who-dd]

133. Menthol,3,trans-1,4-

134. Levomenthol [hsdb]

135. Racementhol [hsdb]

136. Ec 201-939-0

137. Ec 218-690-9

138. Schembl4613

139. Bspbio_003062

140. Kbioss_000785

141. Levomenthol [who-dd]

142. 2-06-00-00052 (beilstein Handbook Reference)

143. 4-06-00-00151 (beilstein Handbook Reference)

144. Mls002207256

145. Divk1c_000820

146. Menthol Racemate [mi]

147. Spectrum1503134

148. Menthol,3r,4s)-(-)-

149. Spbio_000869

150. Gtpl2430

151. Npo-11

152. Dtxsid1020805

153. Dtxsid1022180

154. (-)-menthol, Usp, 97%

155. Hms502i22

156. Kbio1_000820

157. Kbio2_000785

158. Kbio2_003353

159. Kbio2_005921

160. Kbio3_002562

161. Noolisfmxdjskh-kxucptdwsa-

162. (-)-menthol, Analytical Standard

163. Ninds_000820

164. Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1r,3r,4s)-

165. Hms1922g13

166. Hms2092l14

167. Hms3885j18

168. Levomenthol [ep Monograph]

169. Pharmakon1600-01503134

170. Cyclohexanol, 2-isopropyl-5-methyl

171. Nsc62788

172. Zinc1482164

173. L-menthol, >=99%, Fcc, Fg

174. Tox21_111620

175. Tox21_201823

176. Tox21_201919

177. Tox21_202608

178. Tox21_302999

179. Tox21_303028

180. Wln: L6tj Ay1&1 Bq D1

181. Bdbm50318482

182. Ccg-40300

183. Cyclohexanol, 2-isopropyl-5-methyl-

184. Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1alpha,2beta,5alpha)-

185. Nsc758395

186. S4714

187. Akos016842647

188. (1r, 2s, 5r-)-(-)-menthol

189. Bs-3863

190. Db00825

191. Lmpr0102090001

192. Nsc-758395

193. Sdccgmls-0066659.p001

194. (-)-trans-p-methan-cis-3-ol

195. 1-iso Propyl-4-methyl Cyclohexan-2-ol

196. Idi1_000820

197. Wln: L6tj Ay1&1 Dq D1 -l

198. Ncgc00164247-01

199. Ncgc00164247-02

200. Ncgc00164247-03

201. Ncgc00256525-01

202. Ncgc00256561-01

203. Ncgc00259372-01

204. Ncgc00259468-01

205. Ncgc00260156-01

206. D-(-)-phenylglycine Dane Potassium Salt

207. Fema No. 2665, (-)-

208. Smr001306785

209. L-menthol, Natural, >=99%, Fcc, Fg

210. Sbi-0051777.p002

211. N1950

212. S5868

213. Fema No. 2665, (+/-)-

214. Menthol (racemic) 100 Microg/ml In Methanol

215. (+/-)-(1r*,3r*,4s*)-menthol

216. (1r,2s,5r)-(-)-menthol, Synthetic Pellets

217. C00400

218. Cyclohexanol, (1.alpha.,2.beta.,5.alpha.)-

219. D00064

220. D70313

221. (1r,2r,5s)-2-isopropyl-5-methyl-cyclohexanol

222. Ab00052320_02

223. L-menthol

224. Levomenthol

225. Menthomenthol

226. Menthacamphor

227. (1r,2s,5r)-(-)-menthol, >=99%, Sublimed

228. A843308

229. Q407418

230. Q-201316

231. Sr-05000001936-1

232. Sr-05000001936-2

233. (-)-menthol, Primary Pharmaceutical Reference Standard

234. (1r,2s,5r)-(-)-menthol, Reagentplus(r), 99%

235. 2-isopropyl-5-methylcyclohexanol-, (1r,2s,5r)- #

236. Cyclohexanol, [1r-(1.alpha.,2.beta.,5.alpha.)]-

237. (1r,2s,5r)-5-methyl-2-propan-2-yl-cyclohexan-1-ol

238. Z1698549655

239. (1r,2s,5r)-(-)-menthol, Vetec(tm) Reagent Grade, 98%

240. 6c6a4a8c-a054-468c-a1f0-f29e39838cf2

241. (1r, 2s, 5r)-5-methyl-2-(1-methylethyl)cyclohexyl Alcohol

242. Menthol, United States Pharmacopeia (usp) Reference Standard

243. (1r,2s,5r)-rel-5-methyl-2-(1-methylethyl)cyclohexanol

244. L-menthol, Pharmaceutical Secondary Standard; Certified Reference Material

245. (-)-menthol, Puriss., Meets Analytical Specification Of Ph. Eur., Bp, Usp, 98.0-102.0%

246. (1r-(1-.alpha.,2-.beta.,5-.alpha.))-5-methyl-2-(1-methylethyl)cyclohexanol

247. 114376-98-6

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 156.26 g/mol
Molecular Formula C10H20O
XLogP33
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count1
Exact Mass156.151415257 g/mol
Monoisotopic Mass156.151415257 g/mol
Topological Polar Surface Area20.2 Ų
Heavy Atom Count11
Formal Charge0
Complexity120
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

INHALERS CONTAINING MENTHOL COMPRESSED INTO BLOCKS OR CONES ARE COMMONLY USED FOR THE RELIEF OF NASAL CONGESTION, HEADACHE, AND NEURALGIA. IT IS NOW RARELY ADMINISTERED INTERNALLY. /MENTHOL/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 722


TOPICAL ANTIPRURITIC; MEDICATION (VET): HAS BEEN USED AS A MILD LOCAL ANESTHETIC, ANTISEPTIC & INTERNALLY AS A CARMINATIVE & GASTRIC SEDATIVE /MENTHOL/

The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 757


IN LIQUEURS, CONFECTIONERY, PERFUMERY, CIGARETTES, COUGH DROPS, AND NASAL INHALERS /MENTHOL/

The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 757


4.2 Drug Warning

"COOLING" EFFECT OF L-MENTHOL WAS FOUND...TO BE SUPERIOR TO THAT PRODUCED BY OTHER ISOMERS; ODOR AND TASTE, TOO OF L-MENTHOL WERE SUPERIOR, WITH SOME OF THE ISOMERS PRODUCING SHARP, IRRITATING AND DISAGREEABLE PERCEPTIONS.

Osol, A., and R. Pratt. (eds.). The United States Dispensatory. 27th ed. Philadelphia: J.B. Lippincott, 1973., p. 697


4.3 Drug Indication

Used to treat occasional minor irritation, pain, sore mouth, and sore throat as well as cough associated with a cold or inhaled irritants.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. Menthol induces a cooling sensation on the skin upon inhalation, oral ingestion, or topical application by stimulating the cold-sensitive receptors expressed on the skin, without actually causing a drop in the skin temperature.


5.2 Absorption, Distribution and Excretion

...THE PERCENTAGE OF A DOSE OF L-MENTHOL THAT IS EXCRETED COMBINED WITH GLUCURONIC ACID IN THE RABBIT DEPENDS ON THE MAGNITUDE OF THE DOSE; THE LARGER THE DOSE, THE LESS IS THE CONJUGATION.

Opdyke, D.L.J. (ed.). Monographs on Fragrance Raw Materials. New York: Pergamon Press, 1979., p. 519


5.3 Metabolism/Metabolites

L-MENTHOL CONJUGATES READILY IN RABBIT FORMING L-MENTHYL-BETA-D-GLUCURONIDE. ABOUT HALF OF THE L-MENTHOL FED TO RABBITS IS EXCRETED COMBINED WITH GLUCURONIC ACID; THE FATE OF OTHER HALF IS NOT KNOWN, BUT IT IS POSSIBLE THAT RING FISSION OCCURS WITH CONSIDERABLE DEGRADATION OF THE MENTHOL MOLECULE.

Opdyke, D.L.J. (ed.). Monographs on Fragrance Raw Materials. New York: Pergamon Press, 1979., p. 519


IN DOGS, MUCH OXIDATION OF MENTHOL TAKES PLACE AND ONLY ABOUT 5% OF THE DOSE CAN BE RECOVERED IN URINE AS THE GLUCURONIDE. /MENTHOL/

Opdyke, D.L.J. (ed.). Monographs on Fragrance Raw Materials. New York: Pergamon Press, 1979., p. 519


L-MENTHOL WAS RAPIDLY BUT INCOMPLETELY GLUCURONIDATED. THE OUTPUT OF L-MENTHOL GLUCURONIDE WAS INCR IN ALL BUT 1 SUBJECT PRETREATED WITH CIMETIDINE (1 G/DAY FOR 1 WK), AN INHIBITOR OF OXIDATIVE DRUG METABOLISM, & IN ALL SUBJECTS PRETREATED WITH A DRUG-METABOLIZING ENZYME INDUCER, PHENOBARBITONE (60 MG NIGHTLY FOR 10 DAYS).

BELL GD ET AL; BR J CLIN PHARMACOL 12 (2): 274 (1981)


Corynebacterium sp. strain RWM1 grew with (-)-menthol, (-)-menthone and other acyclic monoterpenes as sole carbon sources. Growth on menthol was very slow, with a doubling time of more than 24 h, and was not rapid with (-)-menthone (doubling time 12 h). Concentrations of either carbon source greater than 0.025% inhibited growth. (-)-Menthone-grown cultures transiently accumulated 3,7-dimethyl-6-hydroxyoctanoate during growth, and (-)-menthol-grown cells oxidized (-)-menthol, (-)-menthone, 3,7-dimethyl-6-octanolide and 3,7-dimethyl-6-hydroxyoctanoate. Although neither a menthol oxidase nor a menthol dehydrogenase could be detected in extracts of (-)-menthol- or (-)-menthone-grown cells, an induced NADPH-linked monooxygenase with activity towards (-)-menthone was readily detected. With crude cell extracts, only 3,7-dimethyl-6-hydroxyoctanoate was detected as the reaction product. When the (-)-menthone monooxygenase was separated from an induced 3,7-dimethyl-6-octanolide hydrolase by chromatography on hydroxyapatite, the lactone 3,7-dimethyl-6-octanolide was shown to be the product of oxygenation.

Williams DR, PW Trudgill; Microbiology (Reading) 140 (3): 611-6 (1994)


(-)-Menthol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxyoxane-2-carboxylic acid and p-Menthane-3,-8-diol.

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


5.4 Mechanism of Action

Menthol primarily activates the cold-sensitive TRPM8 receptors in the skin. Menthol, after topical application, causes a feeling of coolness due to stimulation of 'cold' receptors by inhibiting Ca++ currents of neuronal membranes. It may also yield analgesic properties via kappa-opioid receptor agonism.


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