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经验公式(希尔记法):
C10H14O2
化学文摘社编号:
分子量:
166.22
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352002
MDL number:
Assay:
95%
Form:
flakes
InChI
1S/C10H14O2/c1-7(2)8-3-5-9(6-4-8)10(11)12/h5,8H,1,3-4,6H2,2H3,(H,11,12)/t8-/m1/s1
SMILES string
CC(=C)[C@H]1CCC(=CC1)C(O)=O
InChI key
CDSMSBUVCWHORP-MRVPVSSYSA-N
assay
95%
form
flakes
optical activity
[α]20/D −102°, c = 2 in methanol
mp
129-131 °C (lit.)
functional group
carboxylic acid
storage temp.
2-8°C
Quality Level
General description
(S)-(-)-紫苏酸是一种紫苏基衍生物,具有强效的抗微生物和抗癌活性。它可以通过 R-(+)-柠檬烯的生物氧化来制备。
Application
(S)-(−)-紫苏酸 (PA) 可作为起始材料用于制备:,·
- 芳基酰胺,4-(丙-1-烯-2-基)-N-(3-(三氟甲基)苯基)环己基-1-烯-1-甲酰胺和N-(4-(4-氨基-2-甲基苯乙基)-3-甲苯基)-4-(丙-1-烯-2-基)环己基-1-烯-1-甲酰胺,这两种物质可用作体外抗增殖活性剂。
- Machaeriol和大麻素相关化合物,两者用作抗疟剂。
- 三环-β-內酯,先与1-氯-N,N-2-三甲基丙烯胺和酮基丙二酸二甲酯反应,再添加9-氮杂久洛尼定。
Biochem/physiol Actions
通过抑制翻译后半胱氨酸异戊二烯化干扰 p21ras 和其他小 G 蛋白的活性。
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Bioconversion of R-(+)-limonene to perillic acid by the yeast Yarrowia lipolytica.
Ferrara MA, et al.
Brazilian Journal of Microbiology, 44(4), 1075-1080 (2013)
Felix Klotter et al.
Angewandte Chemie (International ed. in English), 54(29), 8547-8550 (2015-06-17)
Short and highly efficient stereoselective syntheses provide machaeriols and cannabinoids in a divergent approach starting from a common precursor, commercially available (S)-perillic acid. Key features of the novel strategy are a stereospecific palladium-catalyzed decarboxylative arylation and a one-pot sequence comprising
Novel N-arylamide derivatives of (S)-perillic acid ((S)-PA): in vitro and in vivo cytotoxicity and antitumor evaluation
Mukhtar YM, et al.
Royal Society of Chemistry Advances, 9(35), 19973-19982 (2019)
Natural product derivatization with β -lactones, β -lactams and epoxides toward `infinite?binders
Jouanneau M, et al.
Tetrahedron, 75(24), 3348-3354 (2019)
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