Terpinen-4-Ol
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Terpinen-4-Ol

Terpinen-4-Ol

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Product Description

Terpinen-4-ol Basic information


Overview Biological activities References


Product Name:

Terpinen-4-ol

Synonyms:

1-isopropyl-4-methyl-cyclohex-3-enol;1-Methyl-4-isopropyl-1-cyclohexen-4-ol;1-methyl-4-isopropyl-1-cyclohexen-4-ol (4-terpineol);1-para-Menthen-4-ol;(+/-)-4-HYDROXY-4-ISOPROPYL-1-METHYL-1-CYCLOHEXENE;4-CARVOMENTHENOL;1-TERPINEN-4-OL;(+/-)-1-ISOPROPYL-4-METHYL-3-CYCLOHEXEN-1-OL

CAS:

562-74-3

MF:

C10H18O

MW:

154.25

EINECS:

209-235-5

Product Categories:

Biochemistry;Terpenes;Terpenes (Others);Monocyclic Monoterpenes;Intermediates & Fine Chemicals;Pharmaceuticals;Alphabetical Listings;C-DFlavors and Fragrances;Certified Natural Products;Flavors and Fragrances;C-D

Mol File:

562-74-3.mol



Terpinen-4-ol Chemical Properties


Melting point 

137-188 °C

alpha 

+25.2°

Boiling point 

212 °C

density 

0.929

FEMA 

2248 | 4-CARVOMENTHENOL

refractive index 

n20/D 1.478

Fp 

175 °F

storage temp. 

-20°C

form 

Liquid

pka

14.94±0.40(Predicted)

Specific Gravity

0.930.9265 (19℃)

color 

Clear colorless to slightly yellow

optical activity

[α]20/D 27°, neat

Water Solubility 

Very slightly soluble

JECFA Number

439

Merck 

3935

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

InChIKey

WRYLYDPHFGVWKC-UHFFFAOYSA-N

CAS DataBase Reference

562-74-3(CAS DataBase Reference)

NIST Chemistry Reference

3-Cyclohexen-1-ol, 4-methyl-1-(1-methylethyl)-(562-74-3)

EPA Substance Registry System

4-Terpineol (562-74-3)


Terpinen-4-ol Safety Information


Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

2

RTECS 

OT0175110

HS Code 

29061990


Terpinen-4-ol Usage


Chemical Properties

colourless or pale yellow liquid

Occurrence

4-Carvomenthenol (dextro) has been reported present in the oil of Cupressus macrocarpa lavender, Spanish origanum, Ledum palustre, Eucalyptus australiana var. A., Thuja occidentalis, etc. The l-form is present in the oil of Eucalyptus dives and in some other essences such as Xanthoxylum rhetsa, together with the racemic form. The racemic form is found in camphor oil. Reported found in fresh apple, apricots, orange juice, peel oils of orange, lemon, grapefruit, tangerines, anise, cinnamon, ginger and nutmeg.

Uses

Shows antioxidant effects. Antiseptic.

Definition

ChEBI: A terpineol that is 1-menthene carrying a hydroxy substituent at position 4.

Taste threshold values

Taste characteristics at 30 ppm: sweet, citrus green with a tropical fruity character.

Anticancer Research

Also this molecule exhibits antitumor effects by apoptotic mechanism. Studies weredone in mice bearing A549 tumor xenografts (Quintans et al. 2013; Kiyan et al.2014).

Chemical Synthesis

One of several terpinenol isomers, depending on the position of the double bond and that of the hydroxyl group, this terpene, whose structure has been defined by Wallach, can be isolated by fractional distillation. It exists in nature as the dextro, levo and racemic isomer; the synthetic product is always optically inactive. The 1-terpineneol or 1-meththyl-4-isopropyl-3-cyclohexen-1-ol has been prepared by Wallach (Burdock, 1997).


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