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(-)-β-caryophyllene

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Origin: China

CasNo: 87-44-5

specification: 99%min

Min order Quantity: 1 /kg

Supply Ability: 50 mt/month

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  • Products Specification
  • Description
  • Property

    CAS No.: 87-44-5 Formula: C15H24 Molecular Weight: 204.35100

    Description

    Caryophyllene , or (−)-β-caryophyllene, is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa, rosemary, and hops. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in an 8-membered ring, both rarities in nature.
    Caryophyllene is one of the chemical compounds that contributes to the spiciness of black pepper. Caryophyllene was shown to be selective agonist of cannabinoid receptor type-2 (CB2) and to exert significant cannabimimetic antiinflammatory effects in mice. Antinociceptive, neuroprotective, anxiolytic and antidepressant and anti-alcoholism activity in in vitro studies and in rodent models have been reported. Because caryophyllene is an FDA-approved food additive and ingested daily with food, it is the first dietary cannabinoid. Whether this compound is able to modulate inflammatory processes in humans via the endocannabinoid system is yet unknown. Caryophyllene does not bind to the centrally expressed cannabinoid receptor type-1 (CB1) and therefore does not exert psychoactive effects.
    The first total synthesis of caryophyllene in 1964 by E.J. Corey was considered one of the classic demonstrations of the possibilities of synthetic organic chemistry at the time.; Caryophyllene oxide, in which the olefin of caryophyllene has become an epoxide, is the component responsible for cannabis identification by drug-sniffing dogs and is also an approved food flavoring.

    Basic Info

    Chemical Name (-)-β-caryophyllene
    Synonyms

    Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R-(1R*,4E,9S*)]-;
    (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene;
    (-)-beta-caryophyllene;

    CAS No. 87-44-5
    Molecular Formula C15H24
    Molecular Weight 204.35100
    PSA 0.00000
    LogP 4.72520

    Properties

    Appearance & Physical State Pale yellow oily liquid with an odor midway between odor of cloves and turpentine.
    Density 0.89 g/cm3
    Boiling Point 268.4ºC at 760 mmHg
    Flash Point 104.9ºC
    Refractive Index n20/D 1.5(lit.)

    Safety Info

    RTECS DT8400000
    Safety Statements 26-36
    HS Code 2902199090
    WGK Germany 1
    Risk Statements R36/37/38

    Synthesis Route

    (1S,9R)-6,10,10-trimethylbicyclo[7.2.0]undec-(5E)-en-2-one+Methyltriphenylphosphonium bromide(-)-β-caryophyllene
    4,5-epithiocaryophyllene(-)-β-caryophyllene
    β-caryophyllene-4β,5α-epoxide(-)-β-caryophyllene+(1S,2S,5R,8R,9R)-1,4,4,8-tetramethyltricyclo[6.3.0.02,5]undecan-9-ol

    Precursor

    (1S,9R)-6,10,10-trimethylbicyclo[7.2.0]undec-(5E)-en-2-one
    Methyltriphenylphosphonium bromide
    β-caryophyllene-4β,5α-epoxide
    4,5-epithiocaryophyllene

    Downstream Product

    (1E,4E,8E)-α-humulene
    (1R,2S,7S,9R)-2,6,10,10-tetramethyltricyclo[7.2.0.02,7]undec-5-ene
    clovene
    β-caryophyllene alcohol

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