potassium hydrate (1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino sulfate

• ChemBase ID: 155264
• Molecular Formular: C10H18KNO10S2
• Molecular Mass: 415.47892
• Monoisotopic Mass: 415.00091946
• SMILES: C=CC/C(=N\OS(=O)(=O)[O-])/S[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O.O.[K+]
• Canonical SMILES: C=CC/C(=N\OS(=O)(=O)[O-])/S[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O.O.[K+]
• InChI: InChI=1S/C10H17NO9S2.K.H2O/c1-2-3-6(11-20-22(16,17)18)21-10-9(15)8(14)7(13)5(4-12)19-10;;/h2,5,7-10,12-15H,1,3-4H2,(H,16,17,18);;1H2/q;+1;/p-1/t5-,7-,8+,9-,10+;;/m1../s1
• InChIKey: IUBVMJHASFBYGW-JMJVLJGISA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium hydrate (1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino sulfate
• IUPAC Traditional name: potassium hydrate sinigrin
• Synonyms: (-)-Sinigrin hydrate

Database IDs

• CAS Number: 3952-98-5
• MDL Number: MFCD00149447
• PubChem SID: 24899488; 24888357; 162249402
• PubChem CID: 23693101

CALCULATED PROPERTIES

• Acid pKa: -3.6183476
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -3.8938658
• LogD (pH = 7.4): -3.893876
• Log P: -3.2342296
• Molar Refractivity: 73.5754 cm^3
• Polarizability: 30.810299 Å^3
• Polar Surface Area: 168.94 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 128 (dec.)(lit.)
• Optical Rotation: [α]20/D -17±1°, c = 1% in H2O

Safety Information

• RTECS: LZ5778000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (TLC)
• Biological Source: from horseradish
• Empirical Formula (Hill Notation): C10H16KNO9S2 · xH2O

DETAILS

Sigma Aldrich - 85440

Biochem/physiol Actions
A β-D-thioglucopyranoside occurring in black mustard seeds and horseradish root. Substrate for thioglucosidase.
Application
Sinigrin, a glucosinolate, is used as a systrate to identify, differentiate and characterize myrosinase(s)/thioglucoside glucohydrolase(s)/thioglucosidase(s). Sinigrin is used as a reference material in procedures for the isolation and identification of glucosinolates.

Sigma Aldrich - S1647

Biochem/physiol Actions
A β-D-thioglucopyranoside occurring in black mustard seeds and horseradish root. Substrate for thioglucosidase.