aescin

{{short description|Main active component in horse chestnut}}

{{cs1 config|name-list-style=vanc}}

{{distinguish|text=aesculin, an unrelated coumarin glycoside also found in horse chestnut}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477243157

| Name=β-Aescin (main component)

| ImageFile=Beta-Aescin.svg

| ImageSize=280

| IUPACName=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)

| SystematicName=(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

| OtherNames=Escin

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4977652

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 505939

| 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

| InChIKey = AXNVHPCVMSNXNP-OXPBSUTMBO

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = AXNVHPCVMSNXNP-OXPBSUTMSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=6805-41-0

| CASNo_Comment = Aescin

| CASNo1_Ref = {{cascite|correct|CAS}}

| CASNo1=11072-93-8

| CASNo1_Comment = β-Aescin

| PubChem=6476031

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG=C08921

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = RUU8G67GQM

| UNII_Comment = Aescin

| UNII1_Ref = {{fdacite|correct|FDA}}

| UNII1 = QYK0D6H79O

| UNII1_Comment = β-Aescin

| 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

}}

|Section2={{Chembox Properties

| C=55 | H=86 | O=24

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

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.{{cite book |last1=Ramelet |first1=Albert-Adrien |title=Sclerotherapy: treatment of varicose and telangiectatic leg veins |publisher=Elsevier Science Health Science |isbn=978-0-323-37726-3 |chapter=Venoactive Drugs|date=24 November 2016 |pages=426–434 |edition=6th}}

Evidence suggests that aescin, especially pure β-aescin, is a safe and effective treatment for short-term treatment of chronic venous insufficiency;{{cite book|last=Goldman, Mitchel P.|title=Sclerotherapy : treatment of varicose and telangiectatic leg veins|date=2016|publisher=Elsevier Science Health Science|others=Weiss, Robert A.,, Guex, Jean-Jerome|isbn=978-0-323-37727-0|edition=6th|location=Amsterdam|oclc=959274899}}{{cite journal|last1=Pittler|first1=Max H.|last2=Ernst|first2=Edzard|date=2012-11-14|title=Horse chestnut seed extract for chronic venous insufficiency|journal=The Cochrane Database of Systematic Reviews|volume=11|issue=11 |pages=CD003230|doi=10.1002/14651858.CD003230.pub4|issn=1469-493X|pmid=23152216|pmc=7144685}} 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.