Umbelliferone

Umbelliferone

Names
IUPAC name 7-Hydroxychromen-2-one
Other names 7-hydroxycoumarin, hydrangine, skimmetine, beta-umbelliferone
Identifiers
CAS Number	93-35-6 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:27510 N
ChEMBL	ChEMBL51628 Y
ChemSpider	4444774 Y
ECHA InfoCard	100.002.038
PubChem	5281426
InChI InChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H Y Key: ORHBXUUXSCNDEV-UHFFFAOYSA-N Y 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
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).
N  (what is YN ?)
Infobox references

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

It absorbs ultraviolet light strongly at several wavelengths. Despite several indications that this chemical is photomutagenic, it is used in sunscreens. Umbelliferone has been reported to have antioxidant properties.

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

Umbelliferone's name is from the umbelliferae family of plants, and the plant family in turn was named for their umbrella-shaped inflorescences, each called an umbel.

Umbelliferone occurs in many familiar plants from the Apiaceae (Umbelliferae) family such as carrot, coriander and garden angelica, as well as in plants from other families, such as the mouse-ear hawkweed (Hieracium pilosella, Asteraceae) or the bigleaf hydrangea (Hydrangea macrophylla, Hydrangeaceae, under the name hydrangine).

It is one of the components of asafoetida, the dried latex from the giant fennel (Ferula communis).

It is also found in Justicia pectoralis (Acanthaceae).

Umbelliferone is a phenylpropanoid and as such is synthesized from L-phenylalanine, which in turn is produced via the shikimate pathway. Phenylalanine is lysated into cinnamic acid, followed by hydroxylation by cinnamate 4-hydroxylase to yield 4-coumaric acid. The 4-coumaric acid is again hydroxylated by cinnamate/coumarate 2-hydroxylase to yield 2,4-dihydroxy-cinnamic acid (umbellic acid) followed by a bond rotation of the unsaturated bond adjacent to the carboxylic acid group. Finally an intramolecular attack from the hydroxyl group of C2' to the carboxylic acid group closes the ring and forms the lactone umbelliferone.