218391
(S)-(-)-紫苏醇
96%
别名:
对薄荷-1,8-二烯-7-醇
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关于此项目
经验公式（希尔记法）:
C10H16O
化学文摘社编号:
分子量:
152.23
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352002
MDL number:
产品名称
(S)-(-)-紫苏醇, 96%
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
SMILES string
CC(=C)[C@H]1CCC(CO)=CC1
InChI key
NDTYTMIUWGWIMO-SNVBAGLBSA-N
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
Quality Level
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Application
(S)-(−)-紫苏醇（POH或4-异丙烯基环己烯甲醇）可用作合成以下物质的起始原料：
- 紫苏醇新糖苷（neoglycoside）衍生物，其可作为潜在的抗癌药。
- （S）-紫苏醇的氨基改性衍生物，其可作为强效的抗增殖剂
- 紫苏醛8,9-环氧化物，其是一种对薄荷烷类衍生物，可作为体内抗肿瘤剂。
General description
(S)-(-)-紫苏醇是一种单萜类化合物，存在于樱桃、薰衣草和留兰香的精油中。 它显示出有效的抗癌活性。
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
存储类别
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
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.
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
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
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