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Merck
CN

218251

马鞭草烯醇

94%

别名:

(-)-4,6,6-三甲基二环[3.1.1]庚-3-烯-2-酮, 马鞭烯酮

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关于此项目

经验公式(希尔记法):
C10H14O
化学文摘社编号:
分子量:
150.22
UNSPSC Code:
85151701
NACRES:
NA.22
PubChem Substance ID:
EC Number:
214-807-2
Beilstein/REAXYS Number:
1907623
MDL number:
Assay:
94%
Form:
liquid
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InChI key

DCSCXTJOXBUFGB-JGVFFNPUSA-N

InChI

1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3/t7-,8+/m0/s1

SMILES string

CC1=CC(=O)[C@H]2C[C@@H]1C2(C)C

assay

94%

form

liquid

optical activity

[α]25/D −130°, c = 10 in ethanol

refractive index

n20/D 1.496 (lit.)

bp

227-228 °C (lit.)

density

0.975 g/mL at 20 °C (lit.)

functional group

ketone

Quality Level

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Application

(1S)-(−)-马鞭草烯酮可与(1R)-(+)-降蒎酮通过酸催化的电环反应,立体选择性地合成手性环型茚衍生物。它也可以作为原料用于制备具有强大抗缺血特性的含4-苯乙烯基骨架的马鞭草烯酮衍生物。

General description

(1S)-(-)-马鞭草烯酮是Suregada zanzibariensis 叶子精油的主要成分之一。 它可以通过(-)-α-蒎烯的生物转化来制备。 (1S)-(-)-马鞭草烯酮对西方松甲虫(WPB)释放的聚集信息素具有对抗作用。

存储类别

10 - Combustible liquids

wgk

WGK 3

flash_point_f

185.0 °F - closed cup

flash_point_c

85 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)


历史批次信息供参考:

分析证书(COA)

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Bioconversion of (+)-and (-)-alpha-pinene to (+)-and (-)-verbenone by plant cell cultures of Psychotria brachyceras and Rauvolfia sellowii.
Limberger RP, et al.
Electronic journal of Biotechnology, 10(4), 500-507 (2007)
Constituents of the essential oil of Suregada zanzibariensis leaves are repellent to the mosquito, Anopheles gambiae ss.
Innocent E, et al.
Journal of Insect Science, 10(1), 57-57 (2010)
Chung Ju et al.
Bioorganic & medicinal chemistry letters, 23(19), 5421-5425 (2013-08-21)
A series of novel (1S)-(-)-verbenone derivatives was synthesized bearing a 4-styryl scaffold. The synthesized compounds were tested for their anti-oxidant, anti-excitotoxic, and anti-ischemic activities. These derivatives significantly reduced oxygen-glucose deprivation-induced neuronal injury and N-methyl-D-aspartic acid-evoked excitotoxicity in cortical neurons. Furthermore
Acetophenone as an anti-attractant for the western pine beetle, Dendroctonus brevicomis LeConte (Coleoptera: Scolytidae).
Journal of Chemical Ecology, 33(4), 817-817 (2007)
Synthesis of (1R)-(+)-nopinone-and (1S)-(-)-verbenone-derived chiral annulated indenes via electrocyclic reactions.
Liu C and Sowa JR.
Tetrahedron Letters, 37(40), 7241-7244 (1996)

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