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β-Caryophyllene

Product Name
β-Caryophyllene
CAS No.
87-44-5
Chemical Name
β-Caryophyllene
Synonyms
CARYOPHYLLENE;β-Caryophyllene;TRANS-CARYOPHYLLENE;B-CARYOPHYLLENE;β-caryophyllen;β-caryophyllen;(E)-Caryophyllene;1-caryophyllene;Bicyclo7.2.0undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-;L-Caryophyllene
CBNumber
CB3414149
Molecular Formula
C15H24
Formula Weight
204.35
MOL File
87-44-5.mol
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β-Caryophyllene Property

Melting point:
<25℃
Boiling point:
129-130 °C/14 mmHg (lit.)
alpha 
D -8 to -9° (chloroform)
Density 
0.901 g/mL at 25 °C (lit.)
vapor pressure 
6Pa at 20℃
refractive index 
n20/D 1.5(lit.)
FEMA 
2252 | BETA-CARYOPHYLLENE
Flash point:
205 °F
storage temp. 
-20°C
solubility 
Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
form 
Liquid
color 
Colourless
Specific Gravity
0.90
Odor
at 100.00 %. sweet woody spice clove dry
Odor Type
spicy
optical activity
[α]23/D 7.5°, neat
Water Solubility 
88μg/L at 20℃
JECFA Number
1324
Merck 
14,1875
BRN 
2044564
Stability:
Light Sensitive
LogP
6.23 at 25℃
CAS DataBase Reference
87-44-5(CAS DataBase Reference)
EPA Substance Registry System
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)- (87-44-5)
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Safety

Risk Statements 
36/37/38
Safety Statements 
26-36-24/25
RIDADR 
UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 
1
RTECS 
DT8400000
HS Code 
29021990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H304May be fatal if swallowed and enters airways

H317May cause an allergic skin reaction

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P331Do NOT induce vomiting.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W225299
Product name
β-Caryophyllene
Purity
natural, ≥80%, FG
Packaging
SAMPLE-K
Price
$56
Updated
2024/03/01
Sigma-Aldrich
Product number
W225299
Product name
β-Caryophyllene
Purity
natural, ≥80%, FG
Packaging
1KG
Price
$117
Updated
2024/03/01
Sigma-Aldrich
Product number
W225299
Product name
β-Caryophyllene
Purity
natural, ≥80%, FG
Packaging
9KG
Price
$526
Updated
2024/03/01
Sigma-Aldrich
Product number
W225299
Product name
β-Caryophyllene
Purity
natural, ≥80%, FG
Packaging
20KG
Price
$656
Updated
2024/03/01
Sigma-Aldrich
Product number
W225207
Product name
β-Caryophyllene
Purity
≥80%, FCC, FG
Packaging
1kg
Price
$79.8
Updated
2024/03/01
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β-Caryophyllene Chemical Properties,Usage,Production

Description

β-Caryophyllene is a sesquiterpene that has been found in plants, including C. sativa, C. indica, and hemp, and has diverse biological activities, including lipid metabolic, antioxidant, anti-neuroinflammatory, anti-proliferative, and antinociceptive properties.

Chemical Properties

β-Caryophyllene has a woody-spicy, dry, clove-like aroma.

Occurrence

Three isomers (α-, β-, and γ-caryophyllene) are found in nature. The β-isomer is the most frequently encountered and most abundant. This sesquiterpene hydrocarbon occurs naturally in approximately 60 essential oils, mainly in that of cloves, from which it was originally isolated. The chemical structure has been thoroughly studied; other studies have been conducted on the isolation and the dipolar moment, as well as on its oxide. Reported found in lime peel oil, lemon, grapefruit, guava fruit, raspberry, black currant, carrot, celery seed, cinnamon bark, anise, nutmeg, cumin seed, ginger, pepper, peppermint oil, mace, laurel and caraway herb.

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.

Definition

ChEBI: A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of <greek beta-caryophyllene, occurring in many essential oils, particularly oil of cloves.

Preparation

Isolated from oil of clove stems and separated from eugenol by treating the oil with 7% sodium carbonate solution, extracting with ether, repeating the carbonate treatment on the concentrated extracts, and finally steam distilling.

Aroma threshold values

Detection at 64 to 90 ppb

Taste threshold values

Taste characteristics at 50 ppm: spicy, pepper-like, woody, camphoraceous with a citrus background.

Synthesis Reference(s)

Journal of the American Chemical Society, 86, p. 485, 1964 DOI: 10.1021/ja01057a040

Air & Water Reactions

Insoluble in water.

Reactivity Profile

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.

Health effects

β-caryophyllene has shown anti-inflammatory activity via decreasing TLR-4, IL-1?, and  TNF-α levels. It attenuated oxidative stress by restoring antioxidant enzymes and repressing lipid peroxidation as well as GSH  depletion.

Fire Hazard

BETA-CARYOPHYLLENE is combustible.

Safety Profile

A skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Carcinogenicity

Caryophyllene showed significant activity as an inducer of the detoxifying enzyme glutathione S-transferase in the mouse liver and small intestine. The ability of natural anticarcinogens to induce detoxifying enzymes has been found to correlate with their activity in the inhibition of chemical carcinogenesis (253a).

β-Caryophyllene Preparation Products And Raw materials

Raw materials

Preparation Products

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β-Caryophyllene Suppliers

Jiangxi Baolin Natural Spices Co.Ltd.
Tel
0796-8180428 13576833965
Fax
0796-8116585
Email
1510355607@qq.com
Country
China
ProdList
118
Advantage
58
Jishui Jianmin Natural Flavor Oil Factory
Tel
0796-8186259 19870606785
Email
1805709358@qq.com
Country
China
ProdList
333
Advantage
58
Jiangxi Baicaoyuan Biotechnology Co. , Ltd.
Tel
0791-82165230 17707911324
Email
2279635539@qq.com
Country
China
ProdList
1387
Advantage
58
Sigma-Aldrich
Tel
021-61415566 800-8193336
Email
orderCN@merckgroup.com
Country
China
ProdList
51456
Advantage
80
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Beijing HwrkChemical Technology Co., Ltd
Tel
010-89508211 18501085097
Fax
010-89508210
Email
sales.bj@hwrkchemical.com
Country
China
ProdList
8418
Advantage
55
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View Lastest Price from β-Caryophyllene manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Beta-Caryophyllene 87-44-5
Price
US $120.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-15
Hebei Weibang Biotechnology Co., Ltd
Product
BETA-CARYOPHYLLENE 87-44-5
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500000kg
Release date
2024-10-30
Hebei Yanxi Chemical Co., Ltd.
Product
BETA-CARYOPHYLLENE 87-44-5
Price
US $30.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20
Release date
2023-09-05

87-44-5, β-CaryophylleneRelated Search:


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  • 4,11,11-trimethyl-8-methylene-,(1r-(1r*,4e,9s*))-bicyclo(7.2.0)undec-4-en
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  • 8-methylene-4,11,11-trimethyl-,(e)-(1r,9s)-(-)-bicyclo(7.2.0)undec-4-en
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