Basic information
- CAS
523-47-7- Standard SMILES
CC1=CC[C@H]2C(C)=CC[C@@H](C(C)C)[C@@H]2C1- InChIKey
USDOQCCMRDNVAH-KKUMJFAQSA-N- Molecular formula
- C15H24
- Average molar mass
- 204.35 g/mol
- Monoisotopic mass
- 204.18780077
Overview
Beta-cadinene is a colorless viscous oil. A constituent of various wood oils such as cade oil, cedarleaf oil.
Names & identifiers
- Preferred name
- beta-Cadinene
- IUPAC
- (1S,4aR,8aS)-4,7-dimethyl-1-propan-2-yl-1,2,4a,5,8,8a-hexahydronaphthalene
- English name
- beta-Cadinene
- Molecular formula
- C15H24
- Molecular weight
- 204.35
Names & synonyms
BETA-CADINENECadina-3,9-dieneCadine-3,9-diene523-47-7(-)-beta-CadineneNCI-C56008.beta.-Cadinenebeta-Cadinene, (-)-CCRIS 5894HSDB 4355Z07LA0GY4JNSC 46152
Show more names
Naphthalene, 1,2,4a,5,8,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, [1S-(1.alpha.,4a.beta.,8a.alpha.)]-cadinenesBETA-CARDININE(1S,4aR,8aS)-1-isopropyl-4,7-dimethyl-1,2,4a,5,8,8a-hexahydronaphthalene(1S)-1,2,4aβ,5,8,8aα-Hexahydro-4,7-dimethyl-1-(1-methylethyl)naphthalene(1S,4aR,8aS)-1,2,4a,5,8,8a-Hexahydro-4,7-dimethyl-1-(1-methylethyl)naphthalene
CADINENE, BETA-NSC-46152BETA-CADINENE [HSDB].BETA.-CADINENE [MI]DTXSID0024713CHEBI:27723(1S,4aR,8aS)-4,7-dimethyl-1-propan-2-yl-1,2,4a,5,8,8a-hexahydronaphthaleneNaphthalene, 1,2,4a,5,8,8a-hexahydro-4,7-dimethyl-1-(1-methylethyl)-, (1S,4aR,8aS)-
Database identifiers
- CAS
523-47-7、5951-61-1- PubChem CID
- 10657
Properties
Computed structural properties
- XLogP
- 4
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 1
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 293
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Wood Dusts & Extracts
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C15 isoprenoids (sesquiterpenes) [PR0103]
OdorSLIGHT PLEASANT ODOR
Density
0.9239 at 68 °F (NTP, 1992) - Less dense than water; will float
0.9239 AT 20 °C/4 °C
0.919-0.925
Color/FormOIL
Solubility
less than 0.1 mg/mL at 64 °F (NTP, 1992)
INSOLUBLE IN WATER; SLIGHTLY SOLUBLE IN ALCOHOL; SOLUBLE IN ACETONE, PETROLEUM ETHER, HOT CHLOROFORM
0.08 mg/L @ 18C (exp)
Insoluble in water
Soluble (in ethanol)
Flash Pointgreater than 230 °F (NTP, 1992)
Boiling Point
525 °F at 760 mmHg ; 300 °F at 20 mmHg (NTP, 1992)
124 °C AT 9 MM HG
273.00 to 276.00 °C. @ 760.00 mm Hg
124 °C (9 mm Hg)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Fire HazardsThis compound is combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: This compound is an eye irritant. (NTP, 1992)
Hazards Summary
10% in petrolatum produced no skin irritation or sensitization in 25 volunteers; Cadinene: LD50 oral (rat) > 5,000 mg/kg; LD50 dermal (rabbit) > 5,000 mg/kg; Emergency treatment: Essential oils; Essential oils can cause CNS depression and aspiration pneumonia after ingestion; Commercial products of essential oils usually contain concentrations of 1% to 20%, and a potentially toxic exposure is 5-15 mL; [HSDB] An eye irritant; [CAMEO] Safe when used as a flavoring agent in food; [JECFA]
Reactive GroupHydrocarbons, Aliphatic Unsaturated
Reactivity ProfileBETA-CADINENE is a sesquiterpene. May react vigorously with strong oxidizing agents. Can react exothermically with reducing agents to release gaseous hydrogen.
Air and Water ReactionsInsoluble in water.
Safety & protection
Fire FightingFires involving this compound should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Uses & manufacturing
Uses
Used in fragrances and flavors; [HSDB] Found in cade oil and cedarleaf oil (wood oils); [CAMEO]
IN FRAGRANCES /CADINENE/
SYNTHETIC FLAVOR INGREDIENT /CADINENE/
Methods of Manufacturing
CAMPBELL, SOFFER; J AM CHEM SOC 64: 417 (1942); CAMPBELL ET AL; J AM CHEM SOC 64: 425 (1942); RAO ET AL, TETRAHEDRON LETTERS 27: 27 (1960); HEROUT ET AL; COLL CZECH CHEM COMMUN 31: 3012 (1966). SYNTHESIS: SOFFER, GUNAY; TETRAHEDRON LETTERS 1355 (1965). /CADINENES/
Use ClassificationFlavoring Agents -> JECFA Flavorings Index
General Manufacturing Information
IN PUBLIC USE SINCE THE 1950S. USE IN FRAGRANCES IN THE USA AMOUNTS TO LESS THAN 4000 POUNDS/YEAR. /CADINENE/
CONCENTRATION IN FINAL PRODUCT (%): SOAP: USUAL 0.01, MAX 0.05; DETERGENT: USUAL 0.001, MAX 0.005; CREAMS, LOTIONS: USUAL 0.01, MAX 0.05; PERFUME: USUAL 0.04, MAX 0.5 /CADINENE/
Applications
General DescriptionColorless viscous oil. A constituent of various wood oils such as cade oil, cedarleaf oil.
Suppliers1 total
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
Additional notes
ChEBI: Beta-cadinene is a cadinene.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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