Aescin

Not to be confused with aesculin, an unrelated coumarin glycoside also found in horse chestnut.

β-Aescin (main component)

Beta-aescin molecular structure
A 3D representation of a beta-aescin molecule
Names
IUPAC name β-D-Glucopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-(22α-(acetyloxy)-16α,24,28-trihydroxy-21β-{[(2Z)-2-methylbut-2-enoyl]oxy}olean-12-en-3β-yl β-D-glucopyranosiduronic acid)
Systematic IUPAC name (2S,3S,4S,5R,6R)-6-{[(3S,4S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-9-(Acetyloxy)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4-hydroxy-3,5-bis{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid
Other names Escin
Identifiers
CAS Number	6805-41-0 Aescin Y 11072-93-8 β-Aescin Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL505939 Y
ChemSpider	4977652 Y
ECHA InfoCard
E number
KEGG	C08921 N
PubChem CID	6476031
UNII	RUU8G67GQM Aescin Y QYK0D6H79O β-Aescin Y
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C55H86O24/c1-10-23(2)46(71)79-43-44(72-24(3)60)55(22-59)26(17-50(43,4)5)25-11-12-30-51(6)15-14-32(52(7,21-58)29(51)13-16-53(30,8)54(25,9)18-31(55)61)75-49-41(77-48-38(67)36(65)34(63)28(20-57)74-48)39(68)40(42(78-49)45(69)70)76-47-37(66)35(64)33(62)27(19-56)73-47/h10-11,26-44,47-49,56-59,61-68H,12-22H2,1-9H3,(H,69,70)/b23-10-/t26-,27+,28+,29+,30+,31+,32-,33+,34+,35-,36-,37+,38+,39-,40-,41+,42-,43-,44-,47-,48-,49+,51-,52+,53+,54+,55-/m0/s1 Y Key: AXNVHPCVMSNXNP-OXPBSUTMSA-N Y InChI=1/C55H86O24/c1-10-23(2)46(71)79-43-44(72-24(3)60)55(22-59)26(17-50(43,4)5)25-11-12-30-51(6)15-14-32(52(7,21-58)29(51)13-16-53(30,8)54(25,9)18-31(55)61)75-49-41(77-48-38(67)36(65)34(63)28(20-57)74-48)39(68)40(42(78-49)45(69)70)76-47-37(66)35(64)33(62)27(19-56)73-47/h10-11,26-44,47-49,56-59,61-68H,12-22H2,1-9H3,(H,69,70)/b23-10-/t26-,27+,28+,29+,30+,31+,32-,33+,34+,35-,36-,37+,38+,39-,40-,41+,42-,43-,44-,47-,48-,49+,51-,52+,53+,54+,55-/m0/s1 Key: AXNVHPCVMSNXNP-OXPBSUTMBO
SMILES CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)CO)OC6C(C(C(C(O6)C(=O)O)OC7C(C(C(C(O7)CO)O)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)CO)OC(=O)C
Properties
Chemical formula	C55H86O24
Molar mass	1131.269 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Aescin or escin is a mixture of saponins with anti-inflammatory, vasoconstrictor and vasoprotective effects found in Aesculus hippocastanum (the horse chestnut). Aescin is the main active component in horse chestnut, and is responsible for most of its medicinal properties. The main active compound of aescin is β-aescin, although the mixture also contains various other components including α-aescin, protoescigenin, barringtogenol, cryptoescin and benzopyrones.

Evidence suggests that aescin, especially pure β-aescin, is a safe and effective treatment for short-term treatment of chronic venous insufficiency; however, more high quality randomized controlled trials are required to confirm the effectiveness. Horse chestnut extract may be as effective and well tolerated as the use of compression stockings.

Mechanism of action

Aescin appears to produce effects through a wide range of mechanisms. It induces endothelial nitric oxide synthesis by making endothelial cells more permeable to calcium ions, and also induces release of prostaglandin F_2α. Other possible mechanisms include serotonin antagonism and histamine antagonism and reduced catabolism of tissue mucopolysaccharides.

External links

• Information on horse chestnut extract from Memorial Sloan-Kettering Cancer Center
• CID 76967409 from PubChem - alpha-Aescin