Skip to Content
MilliporeSigma
All Photos(3)

Key Documents

More Documents

218391

Sigma-Aldrich

(S)-(−)-Perillyl alcohol

96%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C10H16O
CAS Number:
18457-55-1
Molecular Weight:
152.23
MDL number:
MFCD00062995
UNSPSC Code:
12352002
PubChem Substance ID:
24853064
NACRES:
NA.22

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.)

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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)

230.0 °F - closed cup

Flash Point(C)

110 °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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

(1R)-(−)-Myrtenal 98%

Sigma-Aldrich

218243

(1R)-(−)-Myrtenal

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
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
Metabolic engineering of Escherichia coli for limonene and perillyl alcohol production.
Alonso-Gutierrez J, et al.
Metabolic engineering, 19, 33-41 (2013)
Perillyl alcohol as a chemopreventive agent in N-nitrosomethylbenzylamine-induced rat esophageal tumorigenesis.
Liston BW, et al.
Cancer Research, 63(10), 2399-2403 (2003)
Steven P Stratton et al.
Cancer prevention research (Philadelphia, Pa.), 3(2), 160-169 (2010-01-28)
The chemopreventive and antitumor properties of perillyl alcohol (POH) that were studied preclinically indicate that topical POH inhibits both UVB-induced murine skin carcinogenesis (squamous cell tumor models) and 7,12-dimethylbenz(a)anthracene-induced murine melanoma (transgenic models involving tyrosinase-driven Ras). A previous phase 1
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service