22076
(−)-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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关于此项目
经验公式（希尔记法）:
C15H24O
化学文摘社编号:
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
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
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)
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)
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
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