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11584

Sigma-Aldrich

(−)-Terpinen-4-ol

≥95.0% (sum of enantiomers, GC)

Synonym(s):

(R)-1-Isopropyl-4-methyl-3-cyclohexen-1-ol, (R)-p-Menth-1-en-4-ol

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About This Item

Empirical Formula (Hill Notation):
C10H18O
CAS Number:
20126-76-5
Molecular Weight:
154.25
MDL number:
MFCD00167108
UNSPSC Code:
12352002
PubChem Substance ID:
57646932
NACRES:
NA.22

Assay

≥95.0% (sum of enantiomers, GC)

optical activity

[α]20/D -25±6°, neat

optical purity

enantiomeric ratio: ~2:1

refractive index

n20/D 1.479

density

0.934 g/mL at 20 °C

functional group

hydroxyl

SMILES string

CC(C)[C@@]1(O)CCC(C)=CC1

InChI

1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3/t10-/m0/s1

InChI key

WRYLYDPHFGVWKC-JTQLQIEISA-N

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General description

Terpinen-4-ol, a monoterpenoid alcohol, is the key constituent of tea tree (Melaleuca alternifolia) oil.

Application

(-)-Terpinen-4-ol has been used as a standard for the determination of the composition of Lavandula stoechas essential oil by fast gas chromatography-electronic impact ionization/mass spectrometry (FGC-EI/MS).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

174.2 °F - closed cup

Flash Point(C)

79 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH3694
BCCD4270
BCBX2173
BCBR6268V
BCBM5331V

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Evaluation of the anticonvulsant activity of terpinen-4-ol
Sousa, Dami?o P. de, et al
Zeitschrift fur Naturforschung C, 64(1-2), 1-5 (2009)
Zhenbiao Li et al.
Applied microbiology and biotechnology, 104(5), 2163-2178 (2020-01-26)
Tea tree oil (TTO) and its two characteristic components (terpinen-4-ol and 1,8-cineole) have been shown to inhibit Botrytis cinerea growth. In this study, we conducted a transcriptome analysis to determine the effects of TTO and its characteristic components, alone and
Lavandula stoechas essential oil from Spain: Aromatic profile determined by gas chromatography-mass spectrometry, antioxidant and lipoxygenase inhibitory bioactivities.
Carrasco A, et al.
Industrial Crops and Products, 73, 16-27 (2015)
Laura de Fátima Souto Maior et al.
Clinical oral investigations, 23(7), 2837-2848 (2019-05-22)
This study investigated the anti-Candida activity and the Shore A hardness of a tissue conditioner (Softone™) modified by incorporation of terpinen-4-ol and cinnamaldehyde. Agar diffusion, microdilution, and mechanism of action methods were performed to determine to evaluate the antifungal activity
P H Hart et al.
Inflammation research : official journal of the European Histamine Research Society ... [et al.], 49(11), 619-626 (2000-12-29)
To evaluate potential antiinflammatory properties of tea tree oil, the essential oil steam distilled from the Australian native plant, Melaleuca alternifolia. The ability of tea tree oil to reduce the production in vitro of tumour necrosis factor-alpha (TNFalpha), interleukin (IL)-1beta
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