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Merck
CN

22076

Sigma-Aldrich

(−)-氧化石竹烯

≥99.0% (sum of enantiomers, GC)

别名:

β-石竹烯环氧化物, (-)-环氧石竹烯, (1R,4R,6R,10S)-9-亚甲基-4,12,12-三甲基-5-氧杂三环[8.2.0.04,6]十二烷, 反式-石竹烯氧化物, 石竹素

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About This Item

经验公式(希尔记法):
C15H24O
CAS号:
分子量:
220.35
Beilstein:
148213
EC 号:
MDL编号:
UNSPSC代码:
12352212
PubChem化学物质编号:
NACRES:
NA.25

质量水平

方案

≥99.0% (sum of enantiomers, GC)

表单

solid

旋光性

[α]20/D −71±1°, c = 2% in chloroform

mp

61-63 °C
62-63 °C (lit.)

应用

metabolomics
vitamins, nutraceuticals, and natural products

储存温度

2-8°C

SMILES字符串

[H][C@@]12CCC(=C)[C@@]3([H])CC(C)(C)[C@]3([H])CC[C@@]1(C)O2

InChI

1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15-/m1/s1

InChI key

NVEQFIOZRFFVFW-RGCMKSIDSA-N

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一般描述

(−)-石竹烯氧化物或β-石竹烯氧化物(BCPO)是一种天然植物化合物:二环倍半萜,是β-石竹烯(BCP)的氧化衍生物。它有强烈的木材气味。BCPO 通常存在于许多食品和香料植物和精油中,如罗勒、鼠尾草和丁香。它被广泛用作化妆品和食品添加剂。

应用

(−)-石竹烯氧化物已用作:
  • 抗菌剂,研究其对革兰氏阳性、革兰氏阴性及酵母菌的抑菌效果
  • 作为商业标准品,使用气相色谱-火焰电离检测(GC-FID)对地钱提取物的成分进行定量分析。
  • 作为参考标准品,采用气相色谱-质谱联用(GC-MS)技术分析 Achillea ligustica 精油成分的对映体比例。

生化/生理作用

β-石竹烯氧化物是一种有效的抗癌剂,还具有抗氧化、抗炎和抗病毒的特性。它是大鼠和人肝微粒体中药物代谢酶P4503A(CYP3A)活性的强抑制剂。BCPO 还具有镇痛、抗真菌、抗菌和基因保护活性。

其他说明

精心纯化的倍半萜烯;立体选择性重排为烯丙醇;转化为胺

象形图

Exclamation markEnvironment

警示用语:

Warning

危险声明

危险分类

Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2

储存分类代码

11 - Combustible Solids

WGK

WGK 2

闪点(°F)

230.0 °F - closed cup

闪点(°C)

110 °C - closed cup

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves


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Erich Schmidt et al.
Natural product communications, 5(9), 1365-1368 (2010-10-07)
Commercially available aroma samples were evaluated for their olfactory quality by professional perfumers and tested for their antimicrobial activity. Agar diffusion and agar-dilution were used as test methods and a set of two Gram-positive (Staphylococcus aureus and Enterococcus faecalis) and
H.M.R. Hoffmann et al.
Synlett, 337-337 (1991)
Hebaallah Mamdouh Hashiesh et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 140, 111639-111639 (2021-06-07)
The endocannabinoid system (ECS), a conserved physiological system emerged as a novel pharmacological target for its significant role and potential therapeutic benefits ranging from neurological diseases to cancer. Among both, CB1 and CB2R types, CB2R have received attention for its
Jean-Jacques Filippi et al.
Journal of agricultural and food chemistry, 54(17), 6308-6313 (2006-08-17)
The essential oil of Achillea ligustica from Corsica was investigated by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). A total of 82 compounds representing 94.0% of the oil were tentatively identified. The main constituents were the camphane derivatives, representing
H.M.R. Hoffmann et al.
Synlett, 581-581 (1990)

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