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218391

(S)-(−)-Perillyl alcohol

Name: (<I>S</I>)-(−)-Perillyl alcohol
Brand: ALDRICH

96%

Synonym(s):

p-Mentha-1,8-diene-7-ol

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₆O

CAS Number:

18457-55-1

Molecular Weight:

152.23

NACRES:

NA.22

PubChem Substance ID:

24853064

UNSPSC Code:

12352002

MDL number:

MFCD00062995

Assay:

96%

Form:

liquid

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Properties

Quality Level

100

assay

96%

form

liquid

optical activity

[α]22/D −88°, c = 1 in methanol

refractive index

n20/D 1.501 (lit.)

bp

119-121 °C/11 mmHg (lit.)

density

0.96 g/mL at 25 °C (lit.)

functional group

hydroxyl

SMILES string

CC(=C)[C@H]1CCC(CO)=CC1

InChI

1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3/t10-/m1/s1

InChI key

NDTYTMIUWGWIMO-SNVBAGLBSA-N

Description

General description

(S)-(-)-Perillyl alcohol is a monoterpenoid compound found in the essential oils of cherries, lavender and spearmint. It shows potent anticancer activity.

Application

(S)-(−)-Perillyl alcohol (POH or 4-isopropenyl cyclohexene carbinol) can be used as a starting material in the synthesis of:

Perillyl alcohol neoglycoside derivatives as potential anti cancer agents.
Amino-modified derivatives of (S)-perillyl alcohol as potent antiproliferative agents.
Perillaldehyde 8,9-epoxide, a para-menthane class derivative as an in vivo anti-tumor agent.

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pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Synthesis and antiproliferative effects of amino-modified perillyl alcohol derivatives.

Zi Hui et al.

Molecules (Basel, Switzerland), 19(5), 6671-6682 (2014-05-27)

Two series of amino-modified derivatives of (S)-perillyl alcohol were designed and synthesized using (S)-perillaldehyde as the starting material. These derivatives showed increased antiproliferative activity in human lung cancer A549 cells, human melanoma A375-S2 cells and human fibrosarcoma HT-1080 cells comparing

The identification of perillyl alcohol glycosides with improved antiproliferative activity.

Nitin S Nandurkar et al.

Journal of medicinal chemistry, 57(17), 7478-7484 (2014-08-15)

A facile route to perillyl alcohol (POH) differential glycosylation and the corresponding synthesis of a set of 34 POH glycosides is reported. Subsequent in vitro studies revealed a sugar dependent antiproliferative activity and the inhibition of S6 ribosomal protein phosphorylation

Metabolic engineering of Escherichia coli for limonene and perillyl alcohol production.

Alonso-Gutierrez J, et al.

Metabolic engineering, 19, 33-41 (2013)

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Global Trade Item Number

SKU	GTIN
218391-10G	04061837392467
218391-50G	04061837392474