(2S,3S,4S,5R,6R)-6-{[(4S,6bS,8R,9R)-9-(acetyloxy)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(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-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 104973
• Molecular Formular: C55H86O24
• Molecular Mass: 1131.25694
• Monoisotopic Mass: 1130.55090363
• SMILES: C/C=C(\C)/C(=O)OC1[C@@H](C2(CO)C(CC1(C)C)C1=CCC3C4(C)CCC([C@](C)(CO)C4CCC3(C)[C@]1(C)C[C@H]2O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)OC(=O)C
• Canonical SMILES: OC[C@H]1O[C@H](O[C@H]2[C@@H](O[C@@H]([C@H]([C@@H]2O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C(=O)O)OC2CCC3(C([C@@]2(C)CO)CCC2(C3CC=C3[C@@]2(C)C[C@H](C2(C3CC(C)(C)C([C@@H]2OC(=O)C)OC(=O)/C(=C/C)/C)CO)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O
• 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?/m1/s1
• InChIKey: AXNVHPCVMSNXNP-YSYFQUGBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[(4S,6bS,8R,9R)-9-(acetyloxy)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(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-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid; (2S,3S,4S,5R,6R)-6-{[(4S,6bS,8R,9R)-9-(acetyloxy)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2E)-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-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[(4S,6bS,8R,9R)-9-(acetyloxy)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(2-methylbut-2-enoyl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4-hydroxy-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid; (2S,3S,4S,5R,6R)-6-{[(4S,6bS,8R,9R)-9-(acetyloxy)-8-hydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2E)-2-methylbut-2-enoyl]oxy}-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-4-hydroxy-5-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid
• Synonyms: Escin; Aescin; β-ESCIN

Database IDs

• CAS Number: 6805-41-0; 11072-93-8
• EC Number: 229-880-6
• MDL Number: MFCD00076054
• PubChem SID: 24845252; 162091747
• PubChem CID: 16211024

CALCULATED PROPERTIES

• Acid pKa: 3.3492293
• H Acceptors: 22
• H Donor: 13
• LogD (pH = 5.5): -3.0132291
• LogD (pH = 7.4): -4.292402
• Log P: -0.8771895
• Molar Refractivity: 269.7838 cm^3
• Polarizability: 109.871 Å^3
• Polar Surface Area: 388.04 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D -26±3°, c = 5% in methanol

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: KF6296000; KF6298500
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 20/22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H332
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥96.0% (dried material, C); 92-95%
• Grade: purum
• Impurities: ≤6% water

DETAILS

MP Biomedicals - 02157941

(Aescin) Purity: 92-95% White powder.

Sigma Aldrich - 02320

Other Notes
Review1