22075
(−)-trans-Caryophyllene
≥98.0% (sum of enantiomers, GC)
Synonym(s):
β-Caryophyllene, trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene
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About This Item
Empirical Formula (Hill Notation):
C15H24
CAS Number:
Molecular Weight:
204.35
UNSPSC Code:
12352205
NACRES:
NA.22
PubChem Substance ID:
EC Number:
201-746-1
Beilstein/REAXYS Number:
2044564
MDL number:
Assay:
≥98.0% (sum of enantiomers, GC)
Form:
liquid
Quality Level
assay
≥98.0% (sum of enantiomers, GC)
form
liquid
optical activity
[α]20/D −10±1°, neat
refractive index
n20/D 1.499
bp
262-264 °C (lit.)
density
0.902 g/mL at 20 °C (lit.)
storage temp.
2-8°C
SMILES string
[H][C@@]12CC\C(C)=C\CCC(=C)[C@H]1CC2(C)C
InChI
1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1
InChI key
NPNUFJAVOOONJE-GFUGXAQUSA-N
General description
(-)-trans-Caryophyllene, a sesquiterpene, is the major constituent in the essential oil of Mentha longifolia and Commiphora gileadensis. It shows anti-inflammatory, local anaesthetic and antifungal properties. (-)-trans-Caryophyllene also shows potent cytotoxic activity.
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signalword
Danger
hcodes
Hazard Classifications
Asp. Tox. 1 - Skin Sens. 1B
Storage Class
10 - Combustible liquids
wgk
WGK 1
flash_point_f
221.9 °F - closed cup
flash_point_c
105.5 °C - closed cup
ppe
Eyeshields, Gloves
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Seasonal Variation in Content and Chemical Composition of Essential Oils from Leaves of Mentha longifolia Huds.(Lamiaceae).
Niksic H, et al.
Bulletin of the Chemists and Technologists of Bosnia and Herzegovina, 2014, 29-34 null
?-Caryophyllene, a compound isolated from the biblical balm of gilead (Commiphora gileadensis), is a selective apoptosis inducer for tumor cell lines.
Amiel E, et al.
Evidence-Based Complementary and Alternative Medicine : ECAM, 2012 (2012)
Fabienne Hilgers et al.
Microorganisms, 9(1) (2021-01-21)
Terpenoids constitute one of the largest and most diverse groups within the class of secondary metabolites, comprising over 80,000 compounds. They not only exhibit important functions in plant physiology but also have commercial potential in the biotechnological, pharmaceutical, and agricultural