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Home > Encyclopedia > (-)-Caryophyllene

(-)-Caryophyllene

pharmaceutical raw materials
(-)-Caryophyllene structure

(-)-Caryophyllene 

structure
  • CAS No:

    87-44-5

  • Formula:

    C15H24

  • Chemical Name:

    (-)-Caryophyllene

  • Synonyms:

    Bicyclo[7.2.0]undec-4-ene,4,11,11-trimethyl-8-methylene-,(1R,4E,9S)-;Bicyclo[7.2.0]undec-4-ene,4,11,11-trimethyl-8-methylene-,(E)-(1R,9S)-(-)-;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-methylenebicyclo[7.2.0]undec-4-ene;trans-Caryophyllene;Caryophyllene;l-Caryophyllene;β-Caryophyllene;β-Caryophyllen;(-)-β-Caryophyllene;β-Caryophyllene,(-);(-)-Caryophyllene;(-)-trans-Caryophyllene;(-)-E-Caryophyllene;(E)-Caryophyllene;(-)-(E)-Caryophyllene;NSC 11906;Caryophyllene B;trans-β-Caryophyllene;Caryophylline;1407-53-0;8007-38-3;1233519-47-5

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

β-Caryophyllene is a CB2 receptor agonist.


Beta-caryophyllene is a pale yellow oily liquid with an odor midway between odor of cloves and turpentine. (NTP, 1992)|Liquid|Colourless to slightly yellow oily liquid; woody-spicy, dry, clove-like aroma


Beta-caryophyllene is a pale yellow oily liquid with an odor midway between odor of cloves and turpentine. (NTP, 1992)

(-)-Caryophyllene Basic Attributes

204.35

204.35

201-746-1

DTXSID8024739

2902199090

Characteristics

0 Ų

4.72520

Beta-caryophyllene is a pale yellow oily liquid with an odor midway between odor of cloves and turpentine. (NTP, 1992)

0.9052 g/cm3 @ Temp: 17 °C

<25 °C

129.5 °C

205 °F

1.495

less than 1 mg/mL at 70° F (NTP, 1992)

2-8°C

Celiac-rat LD:> 48 mg/kg

In case of high temperature, open flame, strong oxidant is flammable; thermal decomposition is spicy and stimulates smoke

D -8 to -9° (chloroform)

2.00e-10 cm3/molecule*sec

Insoluble in water.

Hydrocarbons, Aliphatic Unsaturated

The unsaturated aliphatic hydrocarbons, such as BETA-CARYOPHYLLENE, are generally much more reactive than the alkanes. Strong oxidizers may react vigorously with them. Reducing agents can react exothermically to release gaseous hydrogen. In the presence of various catalysts (such as acids) or initiators, compounds in this class can undergo very exothermic addition polymerization reactions.

Safety Information

NONH for all modes of transport

1

36/37/38

26-36-24/25

DT8400000

Treasury is ventilated and dry at low temperature; fireproof, high temperature, and stored separately from oxidant

This chemical is combustible. (NTP, 1992)

|Danger|H304 (99.6%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]|P261, P272, P280, P301+P310, P302+P352, P321, P331, P333+P313, P363, P405, and P501|Aggregated GHS information provided by 1995 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this material can be controlled with a dry chemical carbon dioxide or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material under ambient temperatures. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

Toxicity

moderately toxic

Drug Information

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions.They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

SYMPTOMS: This chemical causes irritation of the skin. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits acrid smoke and irritating fumes. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

(E)-beta-caryophyllene

(-)-Caryophyllene Use and Manufacturing

Methods of Manufacturing

It is isolated from clove leaf oil, clove stem oil, cinnamon leaf oil, etc.

Uses

β-Caryophyllene is notable for having a cyclobutane ring, a rarity in nature. β-Caryophyllene is one of the chemical compounds that contributes to the spiciness of black pepper. β-Caryophyllene was shown to selectively bind to the cannabinoid receptor type-2 (CB2) and to exert significant cannabimimetic antiinflammatory effects in mice.


Air care products

Production

25,000 - 100,000 lb

Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-: ACTIVE|Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1S,4E,9R)-: INACTIVE|Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4Z,9S)-: INACTIVE

Food additives -> Flavoring Agents

Flavoring Agents

Computed Properties

Molecular Weight:204.35
XLogP3:4.4
Exact Mass:204.187800766
Monoisotopic Mass:204.187800766
Heavy Atom Count:15
Complexity:293
Undefined Atom Stereocenter Count:2
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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