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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


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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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
Facundo Romani et al.
Current biology : CB, 30(14), 2815-2828 (2020-06-20)
The origin of a terrestrial flora in the Ordovician required adaptation to novel biotic and abiotic stressors. Oil bodies, a synapomorphy of liverworts, accumulate secondary metabolites, but their function and development are poorly understood. Oil bodies of Marchantia polymorpha develop
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

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