23526-45-6

Basic information

• Product Name: VOMIFOLIOL
• Synonyms: VOMIFOLIOL;(1S)-1-Hydroxy-1-[(1E,3R)-3-hydroxy-1-butenyl]-2,6,6-trimethyl-2-cyclohexene-4-one;(S)-4-Hydroxy-4-[(R,E)-3-hydroxy-1-butenyl]-3,5,5-trimethyl-2-cyclohexen-1-one;Blumenol A;2-Cyclohexen-1-one,4-hydroxy-4-[(1E,3R)-3-hydroxy-1-buten-1-yl]-3,5,5-triMethyl-, (4S)-
• CAS NO: 23526-45-6
• Molecular Formula: C₁₃H₂₀O₃
• Molecular Weight: 224.2961
• Mol File: 23526-45-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 115 °C
• Boiling Point: 362.3°Cat760mmHg
• Flash Point: 187.1°C
• Appearance: /
• Density: 1.13g/cm³
• Vapor Pressure: 1.03E-06mmHg at 25°C
• Refractive Index: 1.567
• PKA: 12.72±0.60(Predicted)
• CAS DataBase Reference: VOMIFOLIOL(CAS DataBase Reference)
• NIST Chemistry Reference: VOMIFOLIOL(23526-45-6)
• EPA Substance Registry System: VOMIFOLIOL(23526-45-6)

Safety Data

• Hazardous Substances Data: 23526-45-6(Hazardous Substances Data)

Usage

Description

Vomifoliol, a sesquiterpene alcohol, is a natural chemical compound found in various plants, particularly in the essential oils of ginger and valerian. Known for its potential therapeutic properties, it has been studied for its anti-inflammatory, analgesic, and anti-tumor effects, making it a promising candidate for the development of new pharmaceuticals. Additionally, it has been investigated for its potential as an insect repellent, showcasing its versatility in applications across medicine, agriculture, and pest control.

Uses

Used in Pharmaceutical Industry:
Vomifoliol is used as an anti-inflammatory agent for its ability to reduce inflammation, which can be beneficial in treating various inflammatory conditions.
Vomifoliol is used as an analgesic for its pain-relieving properties, offering a potential alternative for managing pain in different medical scenarios.
Vomifoliol is used as an anti-tumor agent for its potential to inhibit tumor growth, making it a candidate for cancer treatment and research.
Used in Agriculture:
Vomifoliol is used as an insect repellent for its potential to deter pests, offering a natural alternative for crop protection and reducing the need for chemical pesticides.
Used in Pest Control:
Vomifoliol is used as a natural pest deterrent in pest control applications, providing an eco-friendly solution to manage and control various pests.

InChI:InChI=1/C13H20O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,10,14,16H,8H2,1-4H3/b6-5+/t10-,13-/m1/s1

Upstream product

• 39763-33-2 (+)-(S)-dehydrovomifoliol 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 53411-98-6 ethoxy-1' ethoxy-2 pentene-3 nitrile 
• 14203-64-6 7,9,9-trimethyl-1,4-dioxa-spiro[4.5]dec-6-en-8-one 
• 2028-63-9 but-3-yn-2-ol 
• 127-41-3 alpha-ionone 
• 54619-16-8 tetraacetylroseoside 
• 2228-72-0 (±)-2-trans,4-trans-abscisic acid 
• 54835-70-0 (6S,9R)-roseoside 
• 15764-81-5 dehydrovomifoliol 
• 322474-92-0 (R)-4-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-but-3-yn-2-ol 
• 863032-34-2 Acetic acid (E)-(R)-3-[(1S,4S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl]-1-methyl-allyl ester 
• 872003-41-3 Acetic acid (E)-(R)-3-[(R)-4-(tert-butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-1-methyl-allyl ester 
• 863032-50-2 (E)-(R)-4-[(R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-1-enyl]-but-3-en-2-ol 

Downstream Products

• 65620-50-0 (2S,5R,6S)-2,6,10,10-Tetramethyl-1-oxa-spiro[4.5]decan-6-ol 
• 65620-50-0 (2R,5R,6S)-2,6,10,10-Tetramethyl-1-oxa-spiro[4.5]decan-6-ol 
• 65416-59-3 2,10,10-trimethyl-6-methylene-1-oxaspiro[4.5]dec-7-ene 
• 41678-29-9 edulan I 
• 97039-05-9 3,6,9-trihydroxymegastigma-4,7-diene 
• 142173-08-8 6,9-Dihydroxymegastigm-7-en-3-one 
• 70875-03-5 dihydro-oxoactinidol 
• 57461-21-9 (3E)-4-(2,3,6-trimethylphenyl)but-3-en-2-one 
• 79734-43-3 3,5,5-trimethyl-4-[(E)-3-oxo-1-butenyl]-2-cyclohexen-1-one 
• 29210-91-1 1,1,6-trimethyl-3-oxo-1,2,3,4-tetrahydronaphthalene 
• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 697-82-5 2,3,5-trimethylphenol 
• 1125-21-9 2,6,6-trimethyl-2-cyclohexene-1,4-dione 
• 6755-41-5 (2-trans,4-trans)-abscisic acid 

Relevant articles and documents

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Synthesis of optically active vomifoliol and roseoside stereoisomers

A synthesis of optically active vomifoliol stereoisomers 1-4 and their glucosides, roseoside stereoisomers 5-8, was accomplished via α-acetylenic alcohol 11a or 11b effectively prepared by an asymmetric transfer hydrogenation of α,β-acetylenic ketone 10. Simultaneous separation of these stereoisomers by HPLC was also perfomed.

Novel synthesis of degradation products of carotenoids, megastigmatrienone analogues and blumenol-A

Synthesis of 4-alkylidene-3,5,5-trimethylcyclohex-2-enones 7 has been achieved utilising 1,4-conjugate dehydrobromination of allylic bromides 5 as a key step. This chemical transformation is applied to the synthesis of degradation products of carotenoids: megastigmatrienones 7e/1-4,4-methylene-3,5,5-trimethylcyclohex-2-enone 7a, 4-(3-hydroxybutylidene)-3,5,5-trimethylcyclohex-2-enone 9,1,3,7,7-tetramethyl-2-oxabicyclo[4.4.0]dec-5-en-9-one 10a-b and 3,4,7,8-tetrahydro-4,4,7-trimethylnaphthalen-2(6H)-one 15. A novel photoisomerisation of 4-[(Z)-3-acetoxybut-2-enyl]-4-hydroxy-3,5,5-trimethylcyclohex-2-enone 19 to 4-[(E)-3-acetoxybut-2-enyl]-4-hydroxy-3,5,5-trimethylcyclohex-2-enone 20 enables us to synthesise blumenol-A 21.