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Merck

218391

Sigma-Aldrich

(S)-(-)-紫苏醇

96%

别名:

对薄荷-1,8-二烯-7-醇

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About This Item

经验公式(希尔记法):
C10H16O
CAS号:
分子量:
152.23
MDL號碼:
分類程式碼代碼:
12352002
PubChem物質ID:
NACRES:
NA.22

化驗

96%

形狀

liquid

光學活性

[α]22/D −88°, c = 1 in methanol

折射率

n20/D 1.501 (lit.)

bp

119-121 °C/11 mmHg (lit.)

密度

0.96 g/mL at 25 °C (lit.)

SMILES 字串

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 密鑰

NDTYTMIUWGWIMO-SNVBAGLBSA-N

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一般說明

(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。

應用

(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,其是一种薄荷烷类衍生物,可作为体内抗肿瘤剂。

象形圖

Exclamation mark

訊號詞

Warning

危險聲明

危險分類

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

標靶器官

Respiratory system

儲存類別代碼

10 - Combustible liquids

水污染物質分類(WGK)

WGK 3

閃點(°F)

230.0 °F - closed cup

閃點(°C)

110 °C - closed cup

個人防護裝備

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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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
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.
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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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