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
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
C.E. Sowa et al.
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Klaudyna Fidyt et al.
Cancer medicine, 5(10), 3007-3017 (2016-10-30)
Natural bicyclic sesquiterpenes, β-caryophyllene (BCP) and β-caryophyllene oxide (BCPO), are present in a large number of plants worldwide. Both BCP and BCPO (BCP(O)) possess significant anticancer activities, affecting growth and proliferation of numerous cancer cells. Nevertheless, their antineoplastic effects have
Erich Schmidt et al.
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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)
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