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

• ChemBase ID: 68794
• Molecular Formular: C15H16O3
• Molecular Mass: 244.28574
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-methoxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one
• IUPAC Traditional name: 7-methoxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one; osthole
• Synonyms: 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

Database IDs

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

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.3542554
• LogD (pH = 7.4): 3.3542554
• Log P: 3.3542554
• Molar Refractivity: 72.2546 cm^3
• Polarizability: 27.1772 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: methanol: soluble10 mg/mL, clear, colorless
• Apperance: Cryst.; white powder

Safety Information

• Storage Condition: -20°C
• Storage Warning: IRRITANT
• RTECS: GN7700000
• German water hazard class: 1
• TSCA Listed: false
• Storage Temperature: room temp

Pharmacology Properties

• Mechanism of Action: Calcium blocking; Modulates TRH-evoked responses by interacting with the TRH receptor

Product Information

• Purity: ≥95% (HPLC); 95+%; 99.0
• Salt Data: Free Base
• Biological Source: Isol. from Imperatoria ostruthium, Choisya spp., Seseli sibiricum, Prangos bucharica and Peucedanum hispanicum
• Application(s): Analeptic
• Empirical Formula (Hill Notation): C15H16O3

DETAILS

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.

REFERENCES

• 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)