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Caryophyllene oxide

Caryophyllene oxide structure

Caryophyllene oxide 

structure
  • CAS No:

    1139-30-6

  • Formula:

    C15H24O

  • Chemical Name:

    Caryophyllene oxide

  • Synonyms:

    5-Oxatricyclo[8.2.0.04,6]dodecane,4,12,12-trimethyl-9-methylene-,(1R,4R,6R,10S)-;5-Oxatricyclo[8.2.0.04,6]dodecane,4,12,12-trimethyl-9-methylene-,[1R-(1R*,4R*,6R*,10S*)]-;Caryophyllene oxide;Caryophyllene,epoxide;(1R,4R,6R,10S)-4,12,12-Trimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecane;(-)-β-Caryophyllene epoxide;β-Caryophyllene oxide;β-Caryophyllene epoxide;(-)-Epoxydihydrocaryophyllene;(-)-β-Caryophyllene oxide;4β,5α-Epoxycaryophyllene;(-)-Caryophyllene oxide;trans-Caryophyllene oxide;Caryophyllene 4β,5α-oxide;6,7-Epoxy-3(15)-caryophyllene;Caryophyllene 4β,5α-epoxide;105120-46-5;11023-55-5;32095-03-7;52209-95-7

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

Caryophyllene oxide, isolated from from Annona squamosa L. bark., possesses analgesic and anti-inflammatory activity[1].


Colourless solid; Sweet fruity aroma


Caryophyllene oxide is an epoxide. It has a role as a metabolite.

Caryophyllene oxide Basic Attributes

220.35

220.35

214-519-7

S2XU9K448U

DTXSID4051586

29109000

Characteristics

12.53000

4.57

White Crystalline Powder

0.9488 g/cm3 @ Temp: 20 °C

64 °C

138-141 °C @ Press: 10 Torr

>230 °F

1.507

Insoluble in water; Soluble in fat

2-8°C

0.00672mmHg at 25°C

Oral-rat LD50: > 5000 mg/kg

Thermal decomposition spicy irritating smoke

Safety Information

NONH for all modes of transport

2

36/38

26

RP5530000

Xi

The warehouse is low-temperature, ventilated and dry

P305 + P351 + P338

H315-H319

|Warning|H315 (22.11%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, P391, and P501|Aggregated GHS information provided by 249 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

practically nontoxic

BETA-CARYOPHYLLENE OXIDE WAS IDENTIFIED AS COMPONENTS IN THE ESSENTIAL OIL OBTAINED FROM PEUCEDANUM DHANA SEEDS.|ARTEMISA CAMPESTRIS OIL CONTAINS MONOTERPENES, SESQUITERPENES, & OXIDES, WITH AR-CURCUMENE AND CARYOPHYLLENE OXIDE AS MAIN COMPONENTS.|THE ESSENTIAL OIL & THE NONVOLATILE FRACTION FROM THE HEXANE EXTRACTION OF CHRYSANTHEMUM INDICUM AERIAL PARTS WERE ANALYZED AND FOUND TO INCLUDE BETA-CARYOPHYLLENE OXIDE AS ONE OF THE PRIMARY COMPONENTS.|BETA-CARYOPHYLLENE AND CARYOPHYLLENE EPOXIDE WERE PRESENT IN THE OILS OF BOTH LEOCUS AFRICANUS AND ALVESIA ROSMARINIFOLIA PLANTS.|For more Natural Pollution Sources (Complete) data for (-)-BETA-CARYOPHYLLENE EPOXIDE (33 total), please visit the HSDB record page.

Drug Information

14-HYDROXYCARYOPHYLLENE OXIDE WAS ISOLATED FROM THE URINE OF RABBITS TREATED WITH (-)-CARYOPHYLLENE THE X-RAY CRYSTAL STRUCTURE OF 14-HYDROXYCARYOPHYLLENE (AS ACETATE DERIVATIVE) WAS REPORTED. THE METABOLISM WAS SHOWN TO PROGRESS THROUGH (-)-CARYOPHYLLENE OXIDE SINCE THE LATTER COMPOUND ALSO AFFORDED 14-HYDROXYCARYOPHYLLENE AS A METABOLITE.

4,12,12-trimethyl-9-methylene-5-oxatricyclo(8.2.0.04,6)dodecane

Caryophyllene oxide Use and Manufacturing

Uses

POTENTIAL INSECT ATTRACTANT|FRAGRANCE & FLAVORING AGENT|Flavoring Agents -> JECFA Flavorings Index

Production

(1979) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1982) PROBABLY GREATER THAN 9.08X10+5 GRAMS

5-Oxatricyclo[8.2.0.04,6]dodecane, 4,12,12-trimethyl-9-methylene-, (1R,4R,6R,10S)-: ACTIVE|COLLOPS VITTATUS (2.4/TRAP/NIGHT) WAS CAUGHT IN TRAPS CONTAINING CARYOPHYLLENE OXIDE OR MIXTURES CONTAINING THIS COMPOUND.

THE ESSENTIAL OIL OF ARTEMISIA ABSINTHIUM WAS STUDIED USING BOTH THIN-LAYER AND GAS CHROMATOGRAPHY TECHNIQUES. CARYOPHYLLENE OXIDE WAS IDENTIFIED.|ALPINIA ALLUGHAS RHIZOMES YIELDED 0.05% ESSENTIAL OIL BY WATER- AND STEAM-DISTILLATION. COLUMN CHROMATOGRAPHY ON ALUMINA & SILICA GEL AND GAS CHROMATOGRAPHY INDICATED 23.07% CARYOPHYLLENE OXIDE.

Food additives -> Flavoring Agents

Flavoring Agents

Computed Properties

Molecular Weight:220.35
XLogP3:3.6
Hydrogen Bond Acceptor Count:1
Exact Mass:220.182715385
Monoisotopic Mass:220.182715385
Topological Polar Surface Area:12.5
Heavy Atom Count:16
Complexity:330
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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