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218391

Sigma-Aldrich

(S)-(−)-Perillyl alcohol

96%

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Synonym(s):
p-Mentha-1,8-diene-7-ol
Empirical Formula (Hill Notation):
C10H16O
CAS Number:
Molecular Weight:
152.23
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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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This Item
W266418W355704W304522
(S)-(−)-Perillyl alcohol 96%

218391

(S)-(−)-Perillyl alcohol

(S)-(−)-Perillyl alcohol ≥95%, FG

W266418

(S)-(−)-Perillyl alcohol

(S)-(−)-Perillaldehyde ≥92%

W355704

(S)-(−)-Perillaldehyde

(−)−α-Terpineol natural, ≥96%, FCC, FG

W304522

(−)−α-Terpineol

bp

119-121 °C/11 mmHg (lit.)

bp

119-121 °C/11 mmHg (lit.)

bp

104-105 °C/10 mmHg (lit.)

bp

217-218 °C (lit.)

form

liquid

form

-

form

-

form

-

density

0.96 g/mL at 25 °C (lit.)

density

0.96 g/mL at 25 °C (lit.)

density

0.965 g/mL at 25 °C (lit.)

density

0.93 g/mL at 25 °C (lit.)

refractive index

n20/D 1.501 (lit.)

refractive index

n20/D 1.501 (lit.)

refractive index

n20/D 1.508 (lit.)

refractive index

n20/D 1482 (lit.)

optical activity

[α]22/D −88°, c = 1 in methanol

optical activity

[α]20/D −88°, c = 1 in methanol

optical activity

[α]20/D −120°, c = 10 in ethanol

optical activity

-

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

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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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
Luciana Nalone Andrade et al.
International journal of molecular sciences, 17(1) (2016-01-08)
Recent studies have revealed the high cytotoxicity of p-menthane derivatives against human tumor cells. In this study, the substance perillaldehyde 8,9-epoxide, a p-menthane class derivative obtained from (S)-(-)-perillyl alcohol, was selected in order to assess antitumor activity against experimental sarcoma
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
Perillyl alcohol as a chemopreventive agent in N-nitrosomethylbenzylamine-induced rat esophageal tumorigenesis.
Liston BW, et al.
Cancer Research, 63(10), 2399-2403 (2003)
Maria Antonieta Ferrara et al.
Brazilian journal of microbiology : [publication of the Brazilian Society for Microbiology], 44(4), 1075-1080 (2014-04-02)
Perillyl derivatives are increasingly important due to their flavouring and antimicrobial properties as well as their potential as anticancer agents. These terpenoid species, which are present in limited amounts in plants, may be obtained via bioconversion of selected monoterpene hydrocarbons.

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