[1R-(1α,7β,8α)]-1,2,3,5,6,7,8,8a-Octahydro-1,8a-dimethyl-7-(1-methylvinyl)naphthalin
Valencene
Grundinformationen
- CAS
4630-07-3- Standard-SMILES
C=C(C)[C@@H]1CCC2=CCC[C@@H](C)[C@]2(C)C1- InChIKey
QEBNYNLSCGVZOH-NFAWXSAZSA-N- Summenformel
- C15H24
- Durchschnittliche Molmasse
- 204,35 g/mol
- Monoisotopische Masse
- 204,18780077
Überblick
(+)-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.
Namen und Bezeichner
- Bevorzugter Name
- Valencene
- IUPAC
- (3R,4aS,5R)-4a,5-dimethyl-3-prop-1-en-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalene
- Lokaler Name
- [1R-(1α,7β,8α)]-1,2,3,5,6,7,8,8a-Octahydro-1,8a-dimethyl-7-(1-methylvinyl)naphthalin
- Englischer Name
- Valencene
- Summenformel
- C15H24
- Molmasse
- 204.35
Namen und Synonyme
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
Weitere Namen anzeigen
(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
Datenbank-Bezeichner
- CAS
4630-07-3
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 5,2
- Polarare Oberfläche (TPSA)
- 0 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 0
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 15
- Formalladung
- 0
- Komplexität
- 297
Experimentelle und physikochemische Eigenschaften
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
Physikochemische Eigenschaften
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
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.
Gefahrenhinweise
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%)
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- safety_code
- 23-24/25
- Speicherklasse
- 10 - Combustible liquids
- Hazard Classifications
- Asp. Tox. 1
Chemie und Industrie
Verwendung und Herstellung
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
Anwendungen
Beschreibung(+)-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.
VerwendenValencene 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.
Darstellung
synthetischeBy a Wolf–Kishner reduction of nootkatone.
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