Angelicin

Angelicin
Names
Pronunciation ˈeɪn.dʒəlaɪ.sɪn
Preferred IUPAC name
2H-Furo[2,3-h][1]benzopyran-2-one
Other names
Isopsoralen, 2H-furo[2,3-h]chromen-2-one, furo[2,3-h]chromen-2-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.164.795 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C11H6O3/c12-10-4-2-7-1-3-9-8(5-6-13-9)11(7)14-10/h1-6H checkY
    Key: XDROKJSWHURZGO-UHFFFAOYSA-N checkY
  • InChI=1S/C11H6O3/c12-10-4-2-7-1-3-9-8(5-6-13-9)11(7)14-10/h1-6H
  • O=C\2Oc3c1ccoc1ccc3/C=C/2
Properties
C11H6O3
Molar mass 186.166 g·mol−1
Appearance pale yellow crystals [1]
Melting point 134°C
Boiling point 362.6°C
10 mM in DMSO
log P 1.97[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 photosensitizer, vesicant, carcinogen
Flash point 173.1°C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Angelicin is the parent compound in a family of naturally occurring organic compounds known as the angular furanocoumarins. Structurally, it can be considered as benzapyra-2-one fused with a furan moiety in the 7,8-position. Angelicin is commonly found in certain Apiaceae and Fabaceae plant species such as Bituminaria bituminosa. It has a skin permeability coefficient (LogKp) of -2.46.[2] The maximum absorption is observed at 300 nm.[3] The 1HNMR spectrum is available;[1] the infrared and mass spectra of angelicin can be found in this database. The sublimation of angelicin occurs at 120 °C and the pressure of 0.13 Pa.[4] Angelicin is a coumarin.

  1. ^ a b Cite error: The named reference nmr & appearance was invoked but never defined (see the help page).
  2. ^ a b "BioByte". www.biobyte.com. Retrieved 2018-03-15.
  3. ^ Bordin, F.; Dall'Acqua, F.; Guiotto, A. (December 1991). "Angelicins, angular analogs of psoralens: chemistry, photochemical, photobiological and phototherapeutic properties". Pharmacology & Therapeutics. 52 (3): 331–363. doi:10.1016/0163-7258(91)90031-G. ISSN 0163-7258. PMID 1820581.
  4. ^ Böhme, Horst; Severin, Theodor (1957). "Optische Untersuchungen an Cumarinen Mitteilung: Die Ultraviolettabsorption einiger Cumarine pflanzlicher Herkunft". Archiv der Pharmazie. 290 (10): 486–494. doi:10.1002/ardp.19572901010. ISSN 1521-4184. PMID 13471015. S2CID 84020911.