4a,5-Dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene
Basic information
- CAS
4630-07-3- Standard SMILES
C=C(C)C1CCC2=CCCC(C)C2(C)C1- InChIKey
QEBNYNLSCGVZOH-UHFFFAOYSA-N- Molecular formula
- C15H24
- Average molar mass
- 204.35 g/mol
- Monoisotopic mass
- 204.18780077
Overview
valencene has been reported in Frullania tamarisci, Zingiber montanum, and other organisms with data available.
Names & identifiers
- Preferred name
- 4a,5-Dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene
- IUPAC
- 4a,5-dimethyl-3-prop-1-en-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalene
- English name
- Valencene
- Molecular formula
- C15H24
- Molecular weight
- 204.35
Names & synonyms
4a,5-dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene4a,5-dimethyl-3-prop-1-en-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthaleneRefChem:296693Valencene (natural)Oxo-TremorineValencene 854.alpha.,9-octalin4.beta.H,11-diene4.beta.H,5.alpha.-Eremophila-1(10),11-dieneSCHEMBL25137033-Isopropenyl-4a,5-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene #DTXSID60859879
Show more names
Valencen(1R,7R,8aS)-1,2,3,5,6,7,8,8a-Octahydro-1,8a-dimethyl-7-(1-methylethenyl)naphthaleneFEMA 3443(+)-valencene(3R,4aS,5R)-4a,5-Dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthaleneNaphthalene, 1,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-, (1R,7R,8aS)-VALENCENENSC 148969Valencene T
QEBNYNLSCGVZOH-UHFFFAOYSA-NNaphthalene, 1,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-, [1R-(1.alpha.,7.beta.,8a.alpha.)]-Naphthalene, 1,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-, [1S-(1.alpha.,7.alpha.,8a.alpha.)]-MFCD00036657NSC148969AKOS01595561268773-84-2VS-08621
Properties
Computed structural properties
- XLogP
- 5.2
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 1
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 297
Experimental & physicochemical properties
Density0.914-0.919
Solubility
Insoluble in water; soluble in oils
Insoluble (in ethanol)
Boiling Point
123.00 °C. @ 11.00 mm Hg
123 °C (11mm Hg)
Refractive Index1.498-1.508
Physical DescriptionColourless to pale yellow oily liquid
Physicochemical properties
- Boiling point
- 274 °C · 274 °C(lit.)
- Density
- 0.92 g/mL · 0.92 g/mL at 25 °C(lit.)
- FEMA
- 3443 · 3443 | VALENCENE
- refractive index
- 20 · n20/D 1.504(lit.)
- FLAVIS Number
- 1.017 · 01.017 | Valencene
- Flash point
- 230 °F · >230 °F
- storage temp.
- 2 · 2-8°C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- tsca
- TSCA listed
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- safety_code
- 23-24/25
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H304
- Hazard Classifications
- Asp. Tox. 1
- Precautionary statements
- P301+P310-P331-P405-P501
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Uses & manufacturing
Use ClassificationFlavoring Agents -> JECFA Flavorings Index
Applications
Description(+)-Valencene is a sesquiterpene that has been found in C. sativa and is an aromatic component of orange essence oil. (+)-Valencene (50 μM) induces heme oxgenase-1 (HO-1) expression in macrophages and inhibits the expression of inducible nitric oxide synthase (iNOS), the production of nitric oxide (NO), and the release of high-mobility group box-1 (HMGB1) in RAW 264.7 cells stimulated with LPS. It also increases the survival rate in a mouse model of sepsis induced by cecal ligation and puncture. (+)-Valencene has been used in the synthesis of nootkatone .
OccurrenceReported found in citrus fruits, orange peel, orange juice, bitter orange peel oil, lemon peel oil, grapefruit juice, grapefruit peel oil, kumquat peel oil, leaves and stalk of celery, clove stem, Thymus vulgaris L., fresh mango, globe artichoke, cardamom, mangosteen and cocoa.
UsesValencene is a sesquiterpene and an essential oil component found in a variety of plants, and has been shown to have functional antioxidant, antiradical and antimicrobial properties.
Uses(+)-Valencene can be used as a precursor to prepare: (+)-Nootkatone (a sesquiterpene) by dark singlet oxygenation. Benzoyloxyvalencene by reacting with tert-butyl peroxy benzoate via KharaschSosnovsky allylic oxidation method. (+)-Lineariifolianone, a natural product.
General DescriptionValencene is the major sesquiterpene aroma constituent of orange peel oil. It is mainly used as a starting material to synthesize nootkatone, an important flavor compound of grapefruit.
Preparation methods
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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