7-methoxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

• ChemBase编号: 68794
• 分子式: C15H16O3
• 平均质量: 244.28574
• 单一同位素质量: 244.10994437
• SMILES: c1(=O)ccc2ccc(c(c2o1)CC=C(C)C)OC
• Canonical SMILES: COc1ccc2c(c1CC=C(C)C)oc(=O)cc2
• InChI: InChI=1S/C15H16O3/c1-10(2)4-7-12-13(17-3)8-5-11-6-9-14(16)18-15(11)12/h4-6,8-9H,7H2,1-3H3
• InChIKey: MBRLOUHOWLUMFF-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 7-methoxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one
• IUPAC传统名: 7-methoxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one; osthole
• 别名: Osthol; Ostole; Ostol; Osthole; 7-Methoxy-8-prenylcoumarin; Osthol; 7-methoxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one; 7-Methoxy-8-(3-methyl-2-butenyl)coumarin; 7-Methoxy-8-isopentenylcoumarin; Osthole; 7-Methoxy-8-(3-methyl-2-buten-1-yl)-2H-chromen-2-one

登记号

• CAS号: 484-12-8
• MDL号: MFCD00076049
• PubChem SID: 162034524
• PubChem CID: 10228

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 3.3542554
• LogD (pH = 7.4): 3.3542554
• Log P: 3.3542554
• 摩尔折射率: 72.2546 cm^3
• 极化性: 27.1772 Å^3
• 极化表面积: 35.53 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: methanol: soluble10 mg/mL, clear, colorless
• 外观: Cryst.; white powder

安全信息

• 保存条件: -20°C
• 保存注意事项: IRRITANT
• RTECS编号: GN7700000
• 德国WGK号: 1
• TSCA收录: false
• 保存温度: room temp

药理学性质

• 生物活性机理: Calcium blocking; Modulates TRH-evoked responses by interacting with the TRH receptor

产品相关信息

• 纯度: ≥95% (HPLC); 95+%; 99.0
• 成盐信息: Free Base
• 生物来源: Isol. from Imperatoria ostruthium, Choisya spp., Seseli sibiricum, Prangos bucharica and Peucedanum hispanicum
• 应用领域: Analeptic
• Empirical Formula (Hill Notation): C15H16O3

详细说明

Selleck Chemicals - S2337

Research Area: Endocrinology
Biological Activity:
Osthole(Osthol) is a type of coumarin. Osthole is found in cnidium monnieri and several other plants. Osthol may increase androgen,gonadotropin and nitric oxide synthase (NOS) activity. One mouse study indicates osthol had androgen like effect and gonadotropin like effect. [1]

Sigma Aldrich - O9265

Biochem/physiol Actions
Active constituent of Cnidium monnieri, a traditional Chinese medicine used for its anti-inflammatory, analgesic, and anti-lipedemic activities. Dramatically decreased lipid accumulation in a quail model.1 Its neuroprotective effect on MPP(+)-induced cytotoxicity in PC12 cells supports the use of osthole as a therapeutic agent for the treatment of neurodegenerative disorders.2 Suppression of fatty acid synthase expression in HER2-overexpressing breast cancer cells indicates osthole as a promising agent for chemotherapy.3
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. O9265.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

参考文献

• http://www.raysahelian.com/osthole.html
• Hollis, A.F. et al., Aust. J. Chem., 1961, 14, 101, (Osthol hydrochloride)
• Kapoor, S.K. et al., Phytochemistry, 1968, 7, 147, (Osthol)
• Murray, R.D.H. et al., Tetrahedron, 1971, 27, 1247, (synth)
• Bandopadhyay, M. et al., Indian J. Chem., 1974, 12, 23, (synth)
• Raj, K. et al., Indian J. Chem., Sect. B, 1976, 14, 332, (synth)
• Danchul, T.Y. et al., Khim. Prir. Soedin., 1977, 13, 575; Chem. Nat. Compd. (Engl. Transl.), 1977, 13, 479, (Osthol)
• Kumar, R. et al., Phytochemistry, 1978, 17, 2111, (Osthol)
• Murray, R.D.H. et al., The Natural Coumarins, J. Wiley, 1982, (occur)
• Fujioka, T. et al., Chem. Pharm. Bull., 1999, 47, 96-100, (Osthol, pmr, cmr)
• Cai, J.-N. et al., J. Nat. Prod., 2000, 63, 485-488, (Osthol hydrate)