Umbelliferone

Umbelliferone
Names
	Preferred IUPAC name 7-Hydroxy-2H-1-benzopyran-2-one
	Other names 7-hydroxycoumarin, hydrangine, skimmetine, beta-umbelliferone
Identifiers
CAS Number	93-35-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:27510 ;
ChEMBL	ChEMBL51628 ;
ChemSpider	4444774 ;
ECHA InfoCard	100.002.038
PubChem CID	5281426;
UNII	60Z60NTL4G ;
CompTox Dashboard (EPA)	DTXSID5052626 ;
	InChI InChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H Key: ORHBXUUXSCNDEV-UHFFFAOYSA-N ; InChI=1/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H Key: ORHBXUUXSCNDEV-UHFFFAOYAL;
	SMILES c1cc(cc2c1ccc(=O)o2)O;
Properties
Chemical formula	C9H6O3
Molar mass	162.14 g/mol
Appearance	yellowish-white crystalline odorless powder
Melting point	230 °C (446 °F; 503 K) (decomposes)
Magnetic susceptibility (χ)	-88.22·10−6 cm3/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Umbelliferone, also known as 7-hydroxycoumarin, hydrangine, skimmetine, and beta-umbelliferone, is a natural product of the coumarin family.

It absorbs ultraviolet light strongly at several wavelengths. There are some indications that this chemical is antimutagenic,^[1] it is used in sunscreens.^[2] Umbelliferone has been reported to have antioxidant properties.^[3]^[4]

It is a yellowish-white crystalline solid that has a slight solubility in hot water, but high solubility in ethanol.

^ Ohta T, Watanabe K, Moriya M, Shirasu Y, Kada T (1983). "Anti-mutagenic effects of coumarin and umbelliferone on mutagenesis induced by 4-nitroquinoline 1-oxide or UV irradiation in e. Coli". Mutation Research. 117 (1–2): 135–138. doi:10.1016/0165-1218(83)90160-x. PMID 6403855.
^ Du L (2008). "Rational design of a fluorescent hydrogen peroxide probe based on the umbelliferone fluorophore". Tetrahedron Letters. 49 (19): 3045–3048. doi:10.1016/j.tetlet.2008.03.063. PMC 2490821. PMID 19081820.
^ "UMBELLIFERONE". www.chemicalland21.com. Retrieved 21 November 2011.
^ Sim MO, Lee HI, Ham JR, Seo KI, Kim MJ, Lee MK (2015). "Anti-inflammatory and antioxidant effects of umbelliferone in chronic alcohol-fed rats". Nutr Res Pract. 9 (4): 364–369. doi:10.4162/nrp.2015.9.4.364. PMC 4523479. PMID 26244074.

[1] Ohta T, Watanabe K, Moriya M, Shirasu Y, Kada T (1983). "Anti-mutagenic effects of coumarin and umbelliferone on mutagenesis induced by 4-nitroquinoline 1-oxide or UV irradiation in e. Coli". Mutation Research. 117 (1–2): 135–138. doi:10.1016/0165-1218(83)90160-x. PMID 6403855.

[2] Du L (2008). "Rational design of a fluorescent hydrogen peroxide probe based on the umbelliferone fluorophore". Tetrahedron Letters. 49 (19): 3045–3048. doi:10.1016/j.tetlet.2008.03.063. PMC 2490821. PMID 19081820.

[3] "UMBELLIFERONE". www.chemicalland21.com. Retrieved 21 November 2011.

[pmc-4] Sim MO, Lee HI, Ham JR, Seo KI, Kim MJ, Lee MK (2015). "Anti-inflammatory and antioxidant effects of umbelliferone in chronic alcohol-fed rats". Nutr Res Pract. 9 (4): 364–369. doi:10.4162/nrp.2015.9.4.364. PMC 4523479. PMID 26244074.

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