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223190

Sigma-Aldrich

γ-Terpinene

97%

Synonym(s):

gamma-Terpinene, 1-Isopropyl-4-methyl-1,4-cyclohexadiene, p-Mentha-1,4-diene

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About This Item

Empirical Formula (Hill Notation):
C10H16
CAS Number:
99-85-4
Molecular Weight:
136.23
Beilstein:
2038347
EC Number:
202-794-6
MDL number:
MFCD00001537
UNSPSC Code:
12352100
eCl@ss:
39010915
PubChem Substance ID:
24853370
NACRES:
NA.22

vapor density

4.7 (vs air)

Quality Level

200

vapor pressure

~0.7 mmHg ( 20 °C)

Assay

97%

form

liquid

refractive index

n20/D 1.474 (lit.)

bp

182 °C (lit.)

solubility

water: soluble 5%, clear, colorless to faintly yellow

density

0.85 g/mL at 25 °C (lit.)

SMILES string

CC(C)C1=CCC(C)=CC1

InChI

1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,7-8H,5-6H2,1-3H3

InChI key

YKFLAYDHMOASIY-UHFFFAOYSA-N

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General description

γ-Terpinene, volatile essential oil derived from Melaleuca alternifolia, shows antimicrobial properties against various human pathogens. It is also extracted from Lippia multiflora. The antioxidant, anti-inflammatory and anti-proliferative activities of γ-terpinene is studied.

Application

γ-Terpinene can be used as:
  • Hydrogen precursor in the catalytic transfer hydrogenation of silyl enol ethers.
  • A reference compound in the kinetic study of ozonolysis of (E)-β-farnesene.
  • A hydrogen atom donor in the Cr-catalyzed radical cyclization of halo acetals.

Signal Word

Warning

Hazard Statements

H226,H361,H411

Hazard Classifications

Aquatic Chronic 2 - Flam. Liq. 3 - Repr. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

124.9 °F - closed cup

Flash Point(C)

51.6 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB0306
SDBB0305
STBL0513
STBK7773
STBK4672

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FLP-Catalyzed Transfer Hydrogenation of Silyl Enol Ethers
Khan I, et al.
Angewandte Chemie (International Edition in English), 57, 12356-12359 (2018)
Bagora Bayala et al.
PloS one, 9(3), e92122-e92122 (2014-03-26)
This research highlights the chemical composition, antioxidant, anti-inflammatory and anti-proliferative activities of essential oils from leaves of Ocimum basilicum, Ocimum americanum, Hyptis spicigera, Lippia multiflora, Ageratum conyzoides, Eucalyptus camaldulensis and Zingiber officinale. Essential oils were analyzed by gas chromatography-mass spectrometry
Gas-phase reaction of (E)-β-farnesene with ozone: Rate coefficient and carbonyl products
Kourtchev I, et al.
Atmospheric Environment, 43, 3182-3190 (2009)
Chromium-catalyzed radical cyclization of bromo and chloro acetals
MacLeod KC, et al.
Organometallics, 29, 6639-6641 (2010)
Tais Susane Pereira et al.
Journal of ethnopharmacology, 151(2), 852-857 (2013-12-10)
The volatile essential oil derived from the plant Melaleuca alternifolia, also called tea tree oil (TTO), is largely employed for its antimicrobial properties against several human pathogens. It is used in many topical formulations to treat cutaneous infections. Since very
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