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
UNSPSC Code:
12352212
NACRES:
NA.25
PubChem Substance ID:
EC Number:
214-519-7
Beilstein/REAXYS Number:
148213
MDL number:
产品名称
(−)-氧化石竹烯, ≥99.0% (sum of enantiomers, GC)
InChI key
NVEQFIOZRFFVFW-RGCMKSIDSA-N
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
SMILES string
[H][C@@]12CCC(=C)[C@@]3([H])CC(C)(C)[C@]3([H])CC[C@@]1(C)O2
assay
≥99.0% (sum of enantiomers, GC)
form
solid
optical activity
[α]20/D −71±1°, c = 2% in chloroform
mp
61-63 °C
62-63 °C (lit.)
application(s)
metabolomics
vitamins, nutraceuticals, and natural products
storage temp.
2-8°C
Quality Level
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Application
(−)-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。
Biochem/physiol Actions
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。
General description
(−)-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。
Other Notes
精心纯化的倍半萜烯；立体选择性重排为烯丙醇；转化为胺
signalword
Warning
hcodes
Hazard Classifications
Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2
存储类别
11 - Combustible Solids
wgk
WGK 2
flash_point_f
230.0 °F - closed cup
flash_point_c
110 °C - closed cup
ppe
dust mask type N95 (US), Eyeshields, Gloves
C.E. Sowa et al.
Tetrahedron, 49, 4183-4183 (1993)
Linh Thuy Nguyen et al.
Chemico-biological interactions, 278, 123-128 (2017-10-28)
Sesquiterpenes, the main components of plant essential oils, are often taken in the form of folk medicines and dietary supplements. Several sesquiterpenes possess interesting biological activities but they could interact with concurrently administered drugs via inhibition of drug-metabolizing enzymes. Therefore
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.
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)
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