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

CAS: 1139-30-6 Cat. No.: C345753 Summenformel: C₁₅H₂₄O Molekulargewicht: 220.35 EG-Nummer: 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

Übersicht

(−)-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

Synonyme

(-)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

Spezifikationen & Reinheit

≥99%(GC), sum of enantiomers

Biochemische und physiologische Mechanismen

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

Verschickt in

Wet ice

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Reinheit

≥99%(GC)

Namen und Kennungen

• Pubchem Sid: 488191998
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488191998
• Kanonisches Lächeln: 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
• Isomere SMILES: C[C@@]12CC[C@@H]3[C@H](CC3(C)C)C(=C)CC[C@H]1O2
• WGK Deutschland: 2
• RTECS: RP5530000
• Molekulargewicht: 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
    • Klasse Prenol lipids
      • Subclass Sesquiterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Klasse: 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
• Beschreibung: 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

Zugehörige Ziele (menschlich)

TRPV1 Tclin Vanilloid receptor (8273 Activities)

Discover Target: TRPV1

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HL (112 Activities)

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Zugehörige Ziele (nicht menschlich)

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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Wirkungsmechanismen

Chemische und physikalische Eigenschaften

• Empfindlichkeit: Light sensitive
• Schmelzpunkt (°C): 62-63° C (lit.)
• Molekulargewicht: 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

Referenzen

1. Pengfei Yang, Lingqi Kong, Qiongbo Wang, Qiang Liu, Xiujin Duan, Chen Hu, Zhengbo Feng, Qi Yang, Huabo Jv.  (2026)  Analysis of volatile compounds in Aglaia odorata flower extracts with different possessing methods by HS-SPME-GC-MS and E-nose.  Frontiers in Chemistry,      [PMID:41867951] [10.3389/fchem.2026.1746408]