Aesculin

Aesculin

Names
IUPAC name 7-hydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy- 6-(hydroxymethyl)-2-tetrahydropyranyl]oxy}-2-chromenone
Other names Esculetin 6-β-D-glucoside 6,7-dihydroxycoumarin 6-β-D-glucoside 6,7-dihydroxychromen-2-one 6-β-D-glucoside
Identifiers
CAS Number	531-75-9 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL482581 Y
ChemSpider	4444765 Y
ECHA InfoCard	100.007.744
PubChem CID	5281417
UNII	1Y1L18LQAF Y
CompTox Dashboard (EPA)	DTXSID7045318
InChI InChI=1S/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2/t10-,12-,13+,14-,15-/m1/s1 Y Key: XHCADAYNFIFUHF-TVKJYDDYSA-N Y InChI=1/C15H16O9/c16-5-10-12(19)13(20)14(21)15(24-10)23-9-3-6-1-2-11(18)22-8(6)4-7(9)17/h1-4,10,12-17,19-21H,5H2/t10-,12-,13+,14-,15-/m1/s1 Key: XHCADAYNFIFUHF-TVKJYDDYBL
SMILES O=C/3Oc2c(cc(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)c(O)c2)\C=C\3
Properties
Chemical formula	C15H16O9
Molar mass	340.282 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Aesculin, also rendered Æsculin or Esculin, is a coumarin glucoside that naturally occurs in the horse chestnut (Aesculus hippocastanum), California Buckeye (Aesculus californica), Prickly Box (Bursaria spinosa) and in daphnin (the dark green resin of Daphne mezereum). It is also found in dandelion coffee.

Medical uses

As medication, Aesculin is sometimes used as a vasoprotective agent.

Aesculin is also used in a microbiology laboratory to aid in the identification of bacterial species (especially Enterococci and Listeria). In fact, all strains of Group D Streptococci hydrolyze æsculin in 40% bile.

Aesculin hydrolysis test

Aesculin is incorporated into agar with ferric citrate and bile salts (bile aesculin agar). Hydrolysis of the aesculin forms aesculetin (6,7-dihydroxycoumarin) and glucose. The aesculetin forms dark brown or black complexes with ferric citrate, allowing the test to be read.

The bile aesculin agar is streaked and incubated at 37 °C for 24 hours. The presence of a dark brown or black halo indicates that the test is positive. A positive test can occur with Enterococcus, Aerococcus and Leuconostoc. Aesculin will fluoresce under long wave ultraviolet light (360 nm): hydrolysis of aesculin results in loss of this fluorescence.

Enterococcus will often flag positive within four hours of the agar being inoculated.

UV visible spectrum of esculin with a maximum of absorbance at 346 nm

Warnings

Aesculin ingest can produce stomachache, spasms, diarrhea, disorientation, even death at high doses.

References

• Plant poisons: Aesculin
• National Standard Methods MSOP 48 (Bile aesculin agar) and BSOPTP 2 (Aesculin hydrolysis test (UK)).
• C. Michael Hogan (2008) California Buckeye: Aesculus californica, GlobalTwitcher.com, N. Stromberg ed.