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22075

Sigma-Aldrich

(−)-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
Beilstein:
2044564
EC Number:
201-746-1
MDL number:
MFCD00075925
UNSPSC Code:
12352205
PubChem Substance ID:
57647960
NACRES:
NA.22

Quality Level

200

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

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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

Signal Word

Danger

Hazard Statements

H304,H317

Hazard Classifications

Asp. Tox. 1 - Skin Sens. 1B

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

221.9 °F - closed cup

Flash Point(C)

105.5 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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?-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
Pablinny Moreira Galdino et al.
Progress in neuro-psychopharmacology & biological psychiatry, 38(2), 276-284 (2012-05-01)
Spiranthera odoratissima A. St. Hil. (manacá) is used in folk medicine to treat renal and hepatic diseases, stomachache, headaches and rheumatism. A central nervous system (CNS) depressant effect of the hexane fraction from the ethanolic extract of this plant has
Rajesh K Joshi
Natural product communications, 8(3), 401-402 (2013-05-18)
The essential oil composition from the aerial parts of Baccharoides lilacina (Dalzell & A. Gibson) M. R. Almeida was analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). A total of 41 compounds have been identified, representing 97.4% of
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