Basic information
- CAS
555-10-2- Standard SMILES
C=C1C=CC(C(C)C)CC1- InChIKey
LFJQCDVYDGGFCH-UHFFFAOYSA-N- Molecular formula
- C10H16
- Average molar mass
- 136.23 g/mol
- Monoisotopic mass
- 136.12520051
Overview
Beta-phellandrene is one of a pair of phellandrene cyclic monoterpene double-bond isomers in which one double bond is exocyclic (cf. alpha-phellandrene, where both of them are endoocyclic). It has a role as a plant metabolite.
Names & identifiers
- Preferred name
- Beta-Phellandrene
- IUPAC
- 3-methylidene-6-propan-2-ylcyclohexene
- English name
- p-mentha-1(7),2-diene
- Molecular formula
- C10H16
- Molecular weight
- 136.23
Names & synonyms
BETA-PHELLANDRENE555-10-2p-Mentha-1(7),2-diene2-p-Menthadiene3-Isopropyl-6-methylene-1-cyclohexeneCyclohexene, 3-methylene-6-(1-methylethyl)-PHELLANDRENE, BETA3-Methylene-6-(1-methylethyl)cyclohexene4-Isopropyl-1-methylene-2-cyclohexene3-methylidene-6-propan-2-ylcyclohexeneDTXSID4052215CHEBI:48741
Show more names
β-Phellandrene(-)-beta-Phellandrene-β-Phellandrene3-Methylene-6-isopropylcyclohexene3-methylidene-6-propan-2-yl-cyclohexene
NSC-530442KK225M001RefChem:29809DTXCID201079569209-081-93-Isopropyl-6-methylenecyclohex-1-ene.beta.-Phellandreneb-phellandrene
Database identifiers
- CAS
555-10-2- PubChem CID
- 11142
- DTXSID
DTXSID4052215- ChEMBL
CHEMBL444254
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 151
Experimental & physicochemical properties
Chemical ClassesBiological Agents -> Terpenes
FragrancesFragrance Ingredient (beta-Phellandrene) -> IFRA transparency List
LogP4.59
OdorPLEASANT ODOR
TasteBURNING TASTE
Flash Point120 °F.
Boiling Point171.00 to 174.00 °C. @ 760.00 mm Hg
Vapor Density4.68 (AIR= 1)
Vapor Pressure1.59 [mmHg]
Physical Description
Liquid
Oil; [Merck Index] Pleasant odor; [Hawley]
Liquid
Other Experimental Properties
MOBILE OIL; PRACTICALLY INSOL IN WATER; SOL IN ETHER; INDEX OF REFRACTION: 1.4788 @ 20 °C/D; SPECIFIC OPTICAL ROTATION: +65.2 DEG @ 20 °C/D; BP: 171-172 °C @ 760 MM H;; DENSITY: 0.8520 @ 20 °C/4 °C /D-FORM/
Safety & regulation
GHS classification
GHS Classification
Danger
H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P280, P301+P316, P303+P361+P353, P331, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 395 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H304: May be fatal if swallowed and enters airways [Danger Aspiration hazard]
Hazard information
Regulatory Information
Chemical: Cyclohexene, 3-methylene-6-(1-methylethyl)-
Regulation (EC) No 1831/2003 (amended)
Cyclohexene, 3-methylene-6-(1-methylethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexene, 3-methylene-6-(1-methylethyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Cyclohexene, 3-methylene-6-(1-methylethyl)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - Terpinene, terpinolene and phellandrene: Human health tier II assessment
Fire PotentialMODERATE, VIA HEAT, FLAMES, OXIDIZERS.
Hazard Classes and Categories
Flam. Liq. 3 (100%)
Aspiration hazard - category 1
Safety & protection
Fire Fighting ProceduresWATER SPRAY OR FOG, DRY CHEMICAL, CARBON DIOXIDE, FOAM.
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Uses & manufacturing
UsesA naturally occurring essential oil and monoterpene found in certain plants; [HSDB]
U.S. Production2023: 250,000 - <550,000 lb
Industry UsesIntermediates
Methods of Manufacturing
ISOLN OF D-FORM FROM OIL OF WATER FENNEL (PHELLANDRIUM AQUATICUM L, UMBELLIFERAE): BERRY ET AL, J CHEM SOC 1937, 1448. ISOLATION OF L-FORM FROM CANADA BALSAM OIL: MACBETH ET AL, IBID, 1938, 119. STRUCTURE: WALLACH, ANN 343, 28 (1905). SYNTHESIS OF DL-FORM: DEORHA, SAREEN REC TRAV CHIM 82, 137 (1965).
Use ClassificationFragrance Ingredients
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
Cyclohexene, 3-methylene-6-(1-methylethyl)-: ACTIVE
Applications
Uses-Phellandrene is a terpene compound that can be found and extracted from the leaves of eucalyptus radiata. -Phellandrene is also a major constituent of essential oils that have antiproliferative effects in human renal adenocarcinoma and amelanotic melanoma cells.
Upstream & downstream products
Downstream products
Suppliers
Related reactions
2 records
Compound notes
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