| Identification | Back Directory | [Name]
3-CARENE | [CAS]
13466-78-9 | [Synonyms]
carene
3-Karen
3-CARENE
D-CARENE
3-CARVENE
Car-3-ene
FEMA 3821
Isodiprene
S-3-Carene
DELTA-CARENE
3-Carene 90%
DELTA-3-CARENE
CAREN-(3), ROH
3-delta-carene
CARENE, DELTA-3
DELTA-car-3-ene
3-CARENE WITH GC
3-CARENE (DELTA)
delta(Sup3)-Carene
CARENE, Delta-3-(SG)
3-Karen (jfr terpener)
3-Carene,90%,stabilized
delta-3-CARENE, NATURAL
3-Carene, stabilized, 90%
3,7,7-trimethyl-3-norcaren
4,7,7-Trimethyl-3-norcarene
3,7,7-Trimethyl-3-norcarene
3-Carene, stabilized, 90% 1LT
3-Norcarene, 3,7,7-trimethyl-
3-Carene, stabilized, 90% 25ML
3,7,7-trimethyl-bicyclo(4.1.0)hept-3-en
3,7,7-trimethyl-bicyclo[4.1.0]hept-3-en
3,7,7-TRIMETHYLBICYCLO[4.1.0]HEPT-3-ENE
3,7,7-TRIMETHYLBICYCLO[4.1.0]-3-HEPTENE
bicyclo[4.1.0]hept-3-ene,3,7,7-trimethyl-
Bicyclo[4.1.0]hept-3-ene, 3,7,7-trimethyl-
δ-3-carene,3,7,7-trimethylbicyclohept-3-ene
δ3-Carene, 3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene
3,7,7-Trimethylbicyclo(4.1.0)hept-3-ene for synthesis
3-Carene,δ3-Carene, 3,7,7-Trimethylbicyclo[4.1.0]hept-3-ene | [EINECS(EC#)]
236-719-3 | [Molecular Formula]
C10H16 | [MDL Number]
MFCD00001315 | [MOL File]
13466-78-9.mol | [Molecular Weight]
136.23 |
| Chemical Properties | Back Directory | [Definition]
A terpene hydrocarbon with both a 6-member and
3-member ring.
| [Appearance]
liquid | [Melting point ]
25°C | [Boiling point ]
168-169 °C705 mm Hg(lit.)
| [density ]
0.857 g/mL at 25 °C(lit.)
| [FEMA ]
3821 | DELTA-3-CARENE | [refractive index ]
n20/D 1.474(lit.)
| [Fp ]
115 °F
| [storage temp. ]
Flammables area | [solubility ]
Chloroform: Soluble; Methanol: Soluble | [form ]
Liquid | [color ]
Clear colorless to slightly yellow | [Odor]
at 100.00 %. citrus terpenic herbal pine solvent resinous phenolic cypress medicinal woody | [Stability:]
Stable. Flammable. Incompatible with strong oxidizing agents. | [biological source]
synthetic | [Odor Type]
citrus | [Optical Rotation]
[α]20/D +15°, neat | [JECFA Number]
1342 | [Merck ]
1836 | [Major Application]
flavors and fragrances | [Cosmetics Ingredients Functions]
PERFUMING | [InChI]
1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4,8-9H,5-6H2,1-3H3 | [Contact allergens]
Hydroperoxides of D-3-carene are allergens contained
in turpentine. Occupational exposure occurs in painters,
varnishers, or ceramic decoration. The percentage
of D-3-carene is higher in Indonesian than in Portuguese
turpentine. | [InChIKey]
BQOFWKZOCNGFEC-UHFFFAOYSA-N | [SMILES]
CC1=CCC2C(C1)C2(C)C | [LogP]
4.38 | [Uses]
Solvent, intermediate. | [EPA Substance Registry System]
3-Carene (13466-78-9) |
| Hazard Information | Back Directory | [Chemical Properties]
liquid | [General Description]
Colorless liquid with a sweet, turpentine-like odor. Floats on water. | [Reactivity Profile]
3-CARENE may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions. Will attack some forms of plastics [USCG, 1999]. | [Health Hazard]
Inhalation causes headache, confusion, respiratory distress. Ingestion irritates entire digestive system and may injure kidneys; if liquid enters lungs, it causes severe pneumonitis. Contact with eyes or skin causes irritation. | [Description]
(±)-3-Carene is a bicyclic monoterpene found in a variety of plants, including Cannabis.1 It decreases phagocytosis by rat alveolar macrophages when used at a concentration of 0.5 μM and decreases their viability at a concentration of 5 μM.2 (±)-3-Carene increases the expression and activity of alkaline phosphatase in mouse osteoblastic MC3T3-E1 subclone 4 cells, indicating induction of osteoblastic differentiation.3 It also induces calcium formation and increases the expression of osteopontin and type I collagen, which are related to osteoblast mineralization. (±)-3-Carene induces bronchoconstriction in isolated guinea pig lungs when exposed at an air concentration of 3,000 mg/m3.4,5 | [Description]
Hydroperoxides of Δ-3-carene are allergens contained
in turpentine. Occupational exposure occurs in painters,
varnishers, or in ceramic decoration. The percentage
of Δ-3-Carene is higher in Indonesian turpentine
than in Portugese. | [Occurrence]
Reported present in basil oil, bell pepper, bilberry, black currant berry juice and buds, fennel oil, grapefruit
juice, kumquat peel oil, lemon peel oil, lime peel oil (cold pressed and distilled), lovage seed, mandarin peel oil, orange juice, orange
peel oil, orange (bitter) peel oil, tangerine peel oil and other natural products. | [Preparation]
Extracted from the pine tree oil. | [Synthesis Reference(s)]
Tetrahedron Letters, 25, p. 5255, 1984 DOI: 10.1016/S0040-4039(01)81577-X | [Toxics Screening Level]
It is recommended that the Initial Threshold Screening Level (ITSL) for turpentine, along with
select monoterpenes (a-pinene, p-pinene, and A3-carene) be set at 1120 μg/m3 based on an
8-hour averaging time. | [References]
[1] HILLIG K W. A chemotaxonomic analysis of terpenoid variation in Cannabis[J]. Biochemical Systematics and Ecology, 2004, 32 10: Pages 875-891. DOI: 10.1016/j.bse.2004.04.004
[2] ANNE JOHANSSON Margot L. Effects of low concentrations of 3-carene on alveolar macrophages in vitro[J]. Toxicology, 1997, 120 2: Pages 99-104. DOI: 10.1016/s0300-483x(97)03641-x
[3] JONG-GEUN JEONG. Low concentration of 3-carene stimulates the differentiation of mouse osteoblastic MC3T3-E1 subclone 4 cells.[J]. Phytotherapy Research, 2008, 22 1: 18-22. DOI: 10.1002/ptr.2247
[4] L L?STBOM. Mechanisms of 3-carene-induced bronchoconstriction in the isolated guinea pig lung.[J]. Respiration, 1995, 62 3: 130-135. DOI: 10.1159/000196407
[5] LENA L?STBOM . Does airway responsiveness increase after skin sensitisation to 3-carene: a study in isolated guinea pig lungs[J]. Toxicology, 1998, 125 1: Pages 59-66. DOI: 10.1016/s0300-483x(97)00182-0 |
|
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