639-99-6

Basic information

• Product Name: (1S,2S,4R)-(-)-alpha,alpha-dimethyl-1-vinyl-o-menth-8-ene-4-methanol
• Synonyms: (1S,2S,4R)-(-)-alpha,alpha-dimethyl-1-vinyl-o-menth-8-ene-4-methanol;Elemol;elemol,α-elemol;Cyclohexanemethanol, 4-ethenyl-.alpha.,.alpha.,4-trimethyl-3-(1-methylethenyl)-, (1R,3S,4S)-;(1R)-3β-Isopropenyl-α,α,4-trimethyl-4α-vinylcyclohexanemethanol;(1R)-4α-Ethenyl-3β-(1-methylethenyl)-α,α,4-trimethyl-1β-cyclohexanemethanol
• CAS NO: 639-99-6
• Molecular Formula: C₁₅H₂₆O
• Molecular Weight: 222.36634
• EINECS: 211-360-5
• Mol File: 639-99-6.mol

Chemical Properties

• Melting Point: 46 °C
• Boiling Point: 152-156 °C(Press: 17 Torr)
• Appearance: /
• Density: 0.9411 g/cm3
• PKA: 15.18±0.29(Predicted)
• CAS DataBase Reference: (1S,2S,4R)-(-)-alpha,alpha-dimethyl-1-vinyl-o-menth-8-ene-4-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,4R)-(-)-alpha,alpha-dimethyl-1-vinyl-o-menth-8-ene-4-methanol(639-99-6)
• EPA Substance Registry System: (1S,2S,4R)-(-)-alpha,alpha-dimethyl-1-vinyl-o-menth-8-ene-4-methanol(639-99-6)

Safety Data

• Hazardous Substances Data: 639-99-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1S,2S,4R)-(-)-alpha,alpha-dimethyl-1-vinyl-o-menth-8-ene-4-methanol is used as a pharmaceutical compound for its potential biological activity. Its unique molecular structure may contribute to the development of new drugs with specific therapeutic effects.
Used in Fragrance Industry:
(1S,2S,4R)-(-)-alpha,alpha-dimethyl-1-vinyl-o-menth-8-ene-4-methanol is used as a fragrance ingredient for its distinctive sensory attributes. Its unique chemical structure may provide novel scents and enhance the sensory experience in various fragrance products.
Used in Flavor Industry:
(1S,2S,4R)-(-)-alpha,alpha-dimethyl-1-vinyl-o-menth-8-ene-4-methanol is used as a flavoring agent for its potential to impart unique taste profiles. Its distinctive chemical structure may contribute to the creation of innovative flavors in the food and beverage industry.
Research into the biological activity and potential uses of (1S,2S,4R)-(-)-alpha,alpha-dimethyl-1-vinyl-o-menth-8-ene-4-methanol is ongoing, and its diverse applications in various industries may be further explored and expanded in the future.

Upstream product

• 87059-27-6 2-[(1R,3S,4S)-4-(2-Iodo-ethyl)-3-((S)-2-iodo-1-methyl-ethyl)-4-methyl-cyclohexyl]-propan-2-ol 
• 87059-28-7 2-{(1R,3S,4S)-4-Methyl-3-[(S)-1-methyl-2-(2-nitro-phenylselanyl)-ethyl]-4-[2-(2-nitro-phenylselanyl)-ethyl]-cyclohexyl}-propan-2-ol 
• 13065-22-0 11-hydroxy-4α,5α-eudesm-3-one 
• 13085-25-1 trans-Dihydrocarisson-tosylhydrazon 
• 87059-26-5 (S)-2-[(1S,2S,5R)-2-(2-Hydroxy-ethyl)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-cyclohexyl]-propan-1-ol 
• 87059-24-3 (1S,4aS,7R,8aS)-1,4a-Dimethyl-7-(2-methyl-oxiranyl)-octahydro-naphthalen-2-one 
• 87059-23-2 Toluene-4-sulfonic acid 2-((2R,4aS,8aS)-4a,8-dimethyl-7-oxo-decahydro-naphthalen-2-yl)-2-hydroxy-propyl ester 
• 13827-90-2 C₂₉H₄₂O₇S₂ 
• 69366-16-1 (1S,4aS,7R,8aS)-7-(1-Hydroxy-1-methyl-ethyl)-1,4a-dimethyl-decahydro-naphthalen-2-ol 
• 19493-09-5 Methylenetriphenylphosphorane 
• 75-16-1 methylmagnesium bromide 
• 917-64-6 methyl magnesium iodide 
• 83093-41-8 (S)-7-(1,2-Dihydroxy-1-methyl-ethyl)-1,4a-dimethyl-4,4a,5,6-tetrahydro-3H-naphthalen-2-one 
• 83093-43-0 (1S,4aS,7R,8aS)-7-(1,2-Dihydroxy-1-methyl-ethyl)-1,4a-dimethyl-octahydro-naphthalen-2-one 

Downstream Products

• 5951-67-7 (S)-6-ethenyl-6-methyl-1-(1-methylethyl)-3-(1-methylethylidene)cyclohexene 
• 51297-71-3 1-((1R,2S)-5-Isopropylidene-2-methyl-2-vinyl-cyclohexyl)-ethanone 
• 51297-51-9 1-((1R)-2c-methyl-2t-vinyl-5c-isopropenyl-cyclohexyl-(r))-ethanone-⁽¹⁾ 
• 41411-01-2 Gejeron 
• 515-12-8 (1R)-1r-ethyl-2t,4t-diisopropyl-1-methyl-cyclohexane 
• 6617-63-6 Elemanon-6 
• 6617-59-0 (-)-Elemanon-8 
• 51297-60-0 (3S)-4t-ethyl-3r-isopropyl-4c-methyl-cyclohexanone 
• 107307-40-4 (-)-2,3-seco-7α(H)-Eudesmantriol-(2,3,11)-ditritylether 
• 99666-55-4 Acetic acid 1-((1R,3R,4R)-3-acetyl-4-formyl-4-methyl-cyclohexyl)-1-methyl-ethyl ester 
• 51297-25-7 Acetic acid 1-((1R,3R,4S)-3-acetyl-4-methyl-4-vinyl-cyclohexyl)-1-methyl-ethyl ester 
• 80796-88-9 δ-elemene 
• 23665-63-6 β-cyperone 
• 83426-08-8 (-)-O-(3.5-dinitro-benzoyl)elemol 

Relevant articles and documents

Isotopic Labeling Experiments Solve the Hedycaryol Problem

Hedycaryol is a widespread sesquiterpene alcohol and important biosynthetic intermediate toward eudesmols and guaiols. A full NMR assignment for this compound has been hampered because of the unique molecular mechanics of its conformers in complex mixtures. This problem was solved through the enzymatic synthesis of isotopically labeled materials using a mutated plant and a bacterial enzyme for access to both enantiomers of hedycaryol, which also allowed us to follow the stereochemical course of its Cope rearrangement.

Kinetic vs. thermodynamic control in intramolecular diene cyclozirconation: Synthesis of elemol

We predicted (ZINDO) that the major diastereomer from the equilibrating cyclozirconation of the α-terpineol derived diene 1 should be, after oxygenation, the diol 2. We have confirmed this by converting 2 to (+)-elemol 8. The diastereomeric control of the cyclozirconation under kinetic conditions is also striking, providing diol 3.

A STEREOSELECTIVE SYNTHESIS OF (+/-)-ELEMOL VIA AN INTRAMOLECULAR SN2' ESTER ENOLATE ALKYLATION

The monocyclic sesquiterpene, (+/-)-elemol (1) has been synthesized in a highly stereoselective manner by an intramolecular SN2' ester enolate alkylation route.

The chemistry of thujone. VII. Thujone as a chiral synthon for the preparation of sesquiterpenes. Synthesis of β-elemol

An efficient synthesis of β-elemol (4) from thujone (1) is described.The key intermediate 3 is readily prepared and described in previous studies within the syntheses of (+)-carissone (2).