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218391

Sigma-Aldrich

(S)-(−)-Perillyl alcohol

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
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

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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’.

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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
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