7-hydroxy-2H-chromen-2-one

• ChemBase ID: 67538
• Molecular Formular: C9H6O3
• Molecular Mass: 162.14214
• Monoisotopic Mass: 162.03169405
• SMILES: o1c(=O)ccc2ccc(cc12)O
• Canonical SMILES: Oc1ccc2c(c1)oc(=O)cc2
• InChI: InChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H
• InChIKey: ORHBXUUXSCNDEV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-hydroxy-2H-chromen-2-one
• IUPAC Traditional name: umbelliferone; 7-hydroxy-2H-chromen-2-one
• Synonyms: 7-Hydroxy-2-chromenone; 7-Oxycoumarin; Hydrangin; Hydrangine; NSC 19790; Skimmetin; Skimmetine; 7-Hydroxy Coumarin; 7-hydroxy-2H-chromen-2-one; Umbelliferone; 7-Hydroxycoumarin; 7-Hydroxycoumarine; 7-Hydroxycoumarin; Umbelliferone; 7-Hydroxy-2H-1-benzopyran-2-one; 7-hydroxycoumarin; hydranginn; skimmetinn; beta-umbelliferone; Umbelliferone; 7-羟基-2H-1-苯并吡喃-2-酮; 7-羟基香豆素; 伞形酮; 7-羟基香豆素

Database IDs

• CAS Number: 93-35-6
• EC Number: 202-240-3
• MDL Number: MFCD00006878
• Beilstein Number: 127683
• Merck Index: 149847
• PubChem SID: 24889947; 162033273; 24895162
• PubChem CID: 5281426
• CHEBI ID: 27510
• CHEMBL: 51628
• Chemspider ID: 4444774
• Wikipedia Title: Umbelliferone

CALCULATED PROPERTIES

• Acid pKa: 7.83576
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.4778068
• LogD (pH = 7.4): 1.3451345
• Log P: 1.4797943
• Molar Refractivity: 43.5295 cm^3
• Polarizability: 16.31481 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Pale Brown Solid; Yellow powder
• Melting Point: 227-229°C; 228-232°C; 230 °C (dec.)(lit.); 230 °C (decomposes); 230°C; 230-233 °C
• Fluorescence: λex 325 nm; λem 452 nm in 0.1 M citrate pH 3.0

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• RTECS: GN6820000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... STS(412)

Product Information

• Purity: ≥98.0% (HPLC); 95+%; 98%; 98.5; 99%
• Grade: analytical standard
• Suitability: suitable for fluorescence indicator
• Biological Source: Occurs widely in plants including Angelica, Artemisia, Coronilla, Ferula and Ruta spp. Phytoalexin of infected sweet potato
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Antifungal agent; Sunscreen agent
• Empirical Formula (Hill Notation): C9H6O3

DETAILS

MP Biomedicals - 05213622

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02151288

Light yellow crystals

Sigma Aldrich - H24003

Packaging
10, 25, 100 g in poly bottle

Toronto Research Chemicals - H924875

A metabolite of Coumarin. The aglucon of skimmin. Present in many plants.

REFERENCES

• Schilling, et al.: Nature, 221, 664 (1969)
• Indahl, S., et al.: Xenobiotica, 1, 13 (1969)
• Thompson, S.G., et al.: Antimicrob. Agents Chemother., 18, 264 (1969)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 323A; 323C; 325B, (ir)
• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1312C; 1313C; 1315C, (nmr)
• Sethna, S. et al., Org. React. (N.Y.), 1953, 7, 20, (synth)
• Sen, K. et al., J.O.C., 1959, 24, 316, (synth, uv)
• Barnes, C.J. et al., Aust. J. Chem., 1964, 17, 975, (ms)
• das Gupta, A.K. et al., J.C.S.(C), 1969, 29, (synth)
• Hata, K. et al., Chem. Pharm. Bull., 1971, 19, 640, (isol)
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• Ueno, K., Acta Cryst. C, 1985, 41, 1786, (cryst struct)
• Abu-Eittah, R.H. et al., Can. J. Chem., 1985, 63, 1173, (uv)
• Talapatra, B. et al., Indian J. Chem., Sect. B, 1986, 25, 1122, (synth)
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• Gray, A.I. et al., Phytochemistry, 1987, 26, 257, (deriv)
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• Fluorescent indicator.