CAS 1139-30-6

Caryophyllene oxide

Description:

Caryophyllene oxide is a bicyclic sesquiterpene oxide derived from caryophyllene, a natural compound found in various essential oils, particularly those of clove and black pepper. It is characterized by its unique structure, which includes a cyclobutane ring and an epoxide functional group. This compound is typically a colorless to pale yellow liquid with a distinctive, spicy aroma. Caryophyllene oxide is known for its potential therapeutic properties, including anti-inflammatory, antimicrobial, and antioxidant activities, making it of interest in both pharmacological and cosmetic applications. It is also recognized for its role in the flavor and fragrance industry, contributing to the sensory profiles of various products. Additionally, caryophyllene oxide is considered a natural insect repellent and has been studied for its effects on human health, particularly in relation to its interaction with cannabinoid receptors. Its stability and reactivity can vary depending on environmental conditions, influencing its applications in different fields.

Formula: C₁₅H₂₄O

InChI: InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15-/m1/s1

InChI key: InChIKey=NVEQFIOZRFFVFW-RGCMKSIDSA-N

SMILES: C[C@@]12[C@](O1)(CCC(=C)[C@@]3([C@@](CC2)(C(C)(C)C3)[H])[H])[H]

Synonyms:

• (-)-Epoxydihydrocaryophyllene
• (-)-β-Caryophyllene epoxide
• (-)-β-Caryophyllene oxide
• (1R,4R,6R,10S)-4,12,12-Trimethyl-9-methylene-5-oxatricyclo[8.2.0.0^4,6]dodecane
• (1R,4R,6R,10S)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0~4,6~]dodecane
• (1R,4R,6S,10R)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0~4,6~]dodecane
• (1R-(1R*,4R*,6R*,10S*))-4,12,12-Trimethyl-9-methylene-5-oxatricyclo(8.2.0.04,6)dodecane
• (1S,4R,6S,10R)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0~4,6~]dodecane
• (1S,4R,6S,10S)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0~4,6~]dodecane
• (1S,9R)-6,10,10-trimethyl-2-methylidene-5-oxatricyclo[7.2.0.0~4,6~]undecane
• 4,11,11-Trimethyl-8-methylene-5-oxatricyclo(8.2.0.0(4,6))dodecane
• 4,12,12-Trimethyl-9-Methylidene-5-Oxatricyclo[8.2.0.0~4,6~]Dodecane
• 4,12,12-Trimethyl-9-methylene-5-oxatricyclo(8.2.0.04,6)dodecane, (1R,4R,6R,10S)-
• 4β,5α-Epoxycaryophyllene
• 5-Oxatricyclo(8.2.0.0(4,6))dodecane, 4,12,12-trimethyl-9-methylene-, (1R,4R,6R,10S)-
• 5-Oxatricyclo(8.2.0.0(sup 4,6))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,4R,6R,10S)-
• 5-Oxatricyclo[8.2.0.04,6]dodecane, 4,12,12-trimethyl-9-methylene-, [1R-(1R*,4R*,6R*,10S*)]-
• 5-Oxatricyclo[8.2.0.0^4,6]dodecane, 4,12,12-trimethyl-9-methylene-, (1R,4R,6R,10S)-
• 5-Oxatricyclo[8.2.0.0^4,6]dodecane, 4,12,12-trimethyl-9-methylene-, [1R-(1R*,4R*,6R*,10S*)]-
• 5-Oxatricyclo[8.2.O.04.6]Dodecane, 4,12,12-Trimethyl-9-Methylene-, [1R,,4R,6R,10S)]-
• 6,7-Epoxy-3(15)-caryophyllene
• Caryophylene Epoxide
• Caryophylene monoepoxide
• Caryophylene oxide
• Caryophyllene 4β,5α-epoxide
• Caryophyllene 4β,5α-oxide
• Caryophyllene epoxide
• Caryophyllene oxide
• Epoxycaryophyllene
• Hsdb 5466
• [1R-(1R*,4R*,6R*,10S*)]-4,12,12-Trimethyl-9-methylen-5-oxatricyclo[8.2.0.04,6]dodecan
• [1R-(1R*,4R*,6R*,10S*)]-4,12,12-Trimethyl-9-methylen-5-oxatricyclo[8.2.0.04,6]dodecane
• [1R-(1R*,4R*,6R*,10S*)]-4,12,12-Trimethyl-9-methylene-5-oxatricyclo[8.2.0.0.4.6]dodecane
• [1R-(1R*,4R*,6R*,10S*)]-4,12,12-trimetil-9-metilen-5-oxatriciclo[8.2.0.04,6]dodecano
• beta-Caryophyllene oxide
• trans-Caryophyllene oxide

b-Caryophyllene Epoxide

CAS: 1139-30-6

Applications β-Caryophyllene Epoxide, and its derivatives has shown to have microbial transformation and butyrylcholinesterase inhibitory activity. It is also the main active constituent of essential oils obtained from various plants, used for flavoring and fragrances.
References Iqbal, M., et al.: J. Natural Products, 69(10), 1429 (2006); Guo, Y., et al.: Zhongguo Shiyan Fangjixue Zazhi, 19, 110 (2013);

Formula: C₁₅H₂₄O

Color and Shape: White

Molecular weight: 220.35

Ref: TR-C184730

b-Caryophyllene oxide

CAS: 1139-30-6

b-Caryophyllene oxide is a metal chelate that has been shown to have antimicrobial properties against oral pathogens. It has been shown to inhibit voltage-dependent calcium channels and possesses significant cytotoxicity. This compound also inhibits the growth of oral bacteria, including Streptococcus mutans, Actinomyces viscosus, and Porphyromonas gingivalis. b-Caryophyllene oxide has also been shown to inhibit inflammation in experimental models. It has been shown to interact with caryophyllene and other terpenes found in the essential oil of black pepper (Piper nigrum).

Formula: C₁₅H₂₄O

Purity: Min. 95%

Color and Shape: White Off-White Powder

Molecular weight: 220.35 g/mol

Ref: 3D-FC63185

Caryophyllene Oxide

CAS: 1139-30-6

Formula: C₁₅H₂₄O

Molecular weight: 220.36

Ref: ST-EA-CP-C258000

Terpene Mixture 1 2500 µg/mL in Hexane

CAS: 105-87-3, 106-25-2, 1139-30-6, 123-35-3, 124-76-5, 13877-91-3, 23089-26-1, 3790-78-1, 4630-07-3, 470-82-6, 498-15-7, 502-61-4, 76-22-2, 77-53-2, 78-70-6, 79-92-5, 87-44-5, 89-78-1, 89-79-2, 99-83-2, 99-87-6

Color and Shape: Mixture

Ref: 04-S50000473HE