218391
(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:
Molecular Weight:
152.23
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352002
MDL number:
Assay:
96%
Form:
liquid
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
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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signalword
Warning
hcodes
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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Perillyl alcohol as a chemopreventive agent in N-nitrosomethylbenzylamine-induced rat esophageal tumorigenesis.
Liston BW, et al.
Cancer Research, 63(10), 2399-2403 (2003)
Metabolic engineering of Escherichia coli for limonene and perillyl alcohol production.
Alonso-Gutierrez J, et al.
Metabolic engineering, 19, 33-41 (2013)
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