(-)-Caryophyllene oxide - ≥99%(GC), sum of enantiomers , CAS No.1139-30-6

CAS: 1139-30-6 Cat. No.: C345753 Formula: C₁₅H₂₄O Molecular Weight: 220.35 EC Number: 214-519-7

GRADE & PURITY ≥99%(GC), sum of enantiomers

Synonyms

(-)Carophyllene oxide | [1R-(1R*,4R*,6R*,10S*)]- (-)-Epoxydihydrocaryophyllene (-)-<>-Caryophyllene epoxide (-)-<>-Caryophyllene oxide 4,11,11-Trimethyl-8-methylene-5-oxatricyclo(8.2.0.0(4,6))dodecane | C16908 | (-)-Caryophyllene oxide, >=99.0

Storage

Store at 2-8°C,Protected from light,Desiccated

Shipped In

Wet ice

Overview

(−)-Caryophyllene oxide or β-caryophyllene oxide (BCPO) is a natural plant compound, bicyclic sesquiterpene, and oxidation derivative of β-caryophyllene (BCP).  It has a strong wooden odor.  BCPO is commonly found in many food and spice plants and essential oils, such as basil, salvia, and Syzygium cordatum. It is widely used as a cosmetic and food additive. 

Application

(−)-Caryophyllene oxide has been used:

as an antimicrobial agent to study its effects against Gram-positive, Gram-negative and yeast strains 

as a commercial standard to perform quantification analysis of constitutes from Marchantia polymorpha extracts using gas chromatography with flame-ionization detection (GC-FID) 

as a reference standard to analyze the enantiomeric ratios of Achillea ligustica essential oil constituents using gas chromatography-mass spectrometry (GC-MS) 

Specifications

Synonyms

(-)Carophyllene oxide | [1R-(1R*,4R*,6R*,10S*)]- (-)-Epoxydihydrocaryophyllene (-)-<>-Caryophyllene epoxide (-)-<>-Caryophyllene oxide 4,11,11-Trimethyl-8-methylene-5-oxatricyclo(8.2.0.0(4,6))dodecane | C16908 | (-)-Caryophyllene oxide, >=99.0

Specifications & Purity

≥99%(GC), sum of enantiomers

Biochemical and Physiological Mechanisms

β-caryophyllene oxide is a potent anti-cancer agent which also exerts antioxidant, anti-inflammatory, and antiviral properties.It is a strong inhibitor of drug-metabolizing enzyme cytochromes P4503A (CYP3A) activities both in rat and human hepatic microso

Storage

Store at 2-8°C,Protected from light,Desiccated

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%(GC)

Names and Identifiers

Pubchem Sid

488191998

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488191998

Canonical Smiles

CC1(CC2C1CCC3(C(O3)CCC2=C)C)C

IUPAC Name

(1R,4R,6R,10S)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.04,6]dodecane

InChIKey

NVEQFIOZRFFVFW-RGCMKSIDSA-N

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

Isomeric SMILES

C[C@@]12CC[C@@H]3[C@H](CC3(C)C)C(=C)CC[C@H]1O2

WGK Germany

2

RTECS

RP5530000

Molecular Weight

220.35

Reaxy-Rn

148213

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=148213&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Sesquiterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Sesquiterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Sesquiterpenoids
• Alternative Parents: Oxacyclic compounds Epoxides Dialkyl ethers Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Caryophyllane sesquiterpenoid - Sesquiterpenoid - Oxacycle - Organoheterocyclic compound - Ether - Oxirane - Dialkyl ether - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
• External Descriptors: Caryophyllane sesquiterpenoids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TRPV1 Tclin Vanilloid receptor (8273 Activities)

Discover Target: TRPV1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HL (112 Activities)

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Associated Targets(non-human)

Chlamydia pneumoniae (241 Activities)

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Tetranychus urticae (2600 Activities)

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PC-12 (7051 Activities)

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Ileum (29 Activities)

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Jejunum (38 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light sensitive
• Melt Point(°C): 62-63° C (lit.)
• Molecular Weight: 220.350 g/mol
• XLogP3: 3.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 220.183 Da
• Monoisotopic Mass: 220.183 Da
• Topological Polar Surface Area: 12.500 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 330.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1