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Merck

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:
87-44-5
Molecular Weight:
204.35
UNSPSC Code:
12352205
NACRES:
NA.22
PubChem Substance ID:
57647960
EC Number:
201-746-1
Beilstein/REAXYS Number:
2044564
MDL number:
MFCD00075925
Assay:
≥98.0% (sum of enantiomers, GC)
Form:
liquid

Key Documents

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InChI key

NPNUFJAVOOONJE-GFUGXAQUSA-N

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

SMILES string

[H][C@@]12CC\C(C)=C\CCC(=C)[C@H]1CC2(C)C

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

Quality Level

200

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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.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

hcodes

H304,H317

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCG5887
WXBF3469V
BCCC0433
BCBX3595
BCBG0948V

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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
?-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)
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
Linus Svenberg et al.
Plants (Basel, Switzerland), 10(11) (2021-11-28)
In recent work, it was shown that the graminoid plants Cynodon dactylon (Poaceae), Cyperus exaltatus (Cyperaceae), and Panicum repens (Poaceae) have an ovipositional effect on the malaria vector Anopheles gambiae in olfactometric bioassays. In order to get a view of
Getachew E Bokore et al.
Parasites & vectors, 14(1), 552-552 (2021-10-29)
Understanding the ecology and behaviour of disease vectors, including the olfactory cues used to orient and select hosts and egg-laying sites, are essential for the development of novel, insecticide-free control tools. Selected graminoid plants have been shown to release volatile
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