Basic information
- CAS
4630-07-3- Standard SMILES
C=C(C)[C@@H]1CCC2=CCC[C@@H](C)[C@]2(C)C1- InChIKey
QEBNYNLSCGVZOH-NFAWXSAZSA-N- Molecular formula
- C15H24
- Average molar mass
- 204.35 g/mol
- Monoisotopic mass
- 204.18780077
Overview
(+)-valencene is a carbobicyclic compound and sesquiterpene that is 1,2,3,4,4a,5,6,7-octahydronaphthalene which is substituted a prop-1-en-2-yl group at position 3 and by methyl groups at positions 4a and 5 (the 3R,4aS,5R- diastereoisomer). It is a sesquiterpene, a polycyclic olefin and a carbobicyclic compound.
Names & identifiers
- Preferred name
- Valencene
- IUPAC
- (3R,4aS,5R)-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
Valencene(+)-Valencene4630-07-3Valencen(3R,4aS,5R)-4a,5-dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthaleneDTXSID8047052FEMA No. 344396H21P91IGDTXCID6027052CHEBI:61700NSC-1489694Betah,5alpha-eremophila-1(10),11-diene
Show more names
(1R,7R,8aS)-1,2,3,5,6,7,8,8a-Octahydro-1,8a-dimethyl-7-(1-methylethenyl)naphthaleneFEMA 3443NSC 148969Valencene TVALENCENE 85
Naphthalene, 1,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-, (1R,7R,8aS)-Naphthalene, 1,2,3,5,6,7,8,8A-octahydro-1,8A-dimethyl-7-(1-methylethenyl)-, (1R-(1alpha,7beta,8aalpha))-RefChem:901568225-047-6Valencene (Standard)MFCD00075884Valencene (Technical Grade)ent-7betaH-eremophila-10(1),11-diene
Database identifiers
- CAS
4630-07-3- PubChem CID
- 9855795
- DTXSID
DTXSID8047052- ChEMBL
CHEMBL3186909
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
SpringerMaterials PropertiesOptical coefficient
FragrancesFragrance Ingredient (Valencene) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.914-0.919
Flavoring AgentsEU Flavoring substances
Solubility
Insoluble in water; soluble in oils
Insoluble (in ethanol)
Boiling Point123 °C (11mm Hg)
Refractive Index1.498-1.508
Physical DescriptionColourless to pale yellow oily liquid
Physicochemical properties
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1685) of reports.
Danger
H304 (98.5%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]
P301+P316, P331, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1685 reports by companies from 9 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Naphthalene, 1,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-, [1R-(1.alpha.,7.beta.,8a.alpha.)]-
Regulation (EC) No 1831/2003 (amended)
Naphthalene, 1,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-, (1R,7R,8aS)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAsp. Tox. 1 (98.5%)
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
Uses & manufacturing
Use Classification
Fragrance Ingredients
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing InformationNaphthalene, 1,2,3,5,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-, (1R,7R,8aS)-: ACTIVE
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
5 records
Compound notes
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