(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(3-hydroxyprop-1-en-1-yl)-2-methoxyphenoxy]oxane-3,4,5-triol

• ChemBase ID: 126681
• Molecular Formular: C16H22O8
• Molecular Mass: 342.34108
• Monoisotopic Mass: 342.13146766
• SMILES: O(c1c(OC)cc(/C=C/CO)cc1)[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO
• Canonical SMILES: OC/C=C/c1ccc(c(c1)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C16H22O8/c1-22-11-7-9(3-2-6-17)4-5-10(11)23-16-15(21)14(20)13(19)12(8-18)24-16/h2-5,7,12-21H,6,8H2,1H3/t12-,13-,14+,15-,16-/m1/s1
• InChIKey: SFLMUHDGSQZDOW-IBEHDNSVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(3-hydroxyprop-1-en-1-yl)-2-methoxyphenoxy]oxane-3,4,5-triol; (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(3-hydroxyprop-1-en-1-yl)-2-methoxyphenoxy]oxane-3,4,5-triol; coniferin
• Synonyms: ? β-D-Glucopyranoside 4-(3-hydroxy-1-propenyl)-2-methoxyphenyl; ? Coniferyl alcohol β-D-glucoside; Coniferin; Coniferin; 4-(3-Hydroxy-1-propen-1-yl)-2-methoxyphenyl β-Glucopyranoside; 4-Hydroxy-3-methoxy-1-(γ-hydroxypropenyl)benzene-4-D-glucoside; Abietin; Coniferosid; Coniferoside; Laricin

Database IDs

• CAS Number: 531-29-3
• PubChem SID: 162221011
• PubChem CID: 5280372
• Chemspider ID: 4444067
• Wikipedia Title: Coniferin

CALCULATED PROPERTIES

• Acid pKa: 12.199851
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -0.91349304
• LogD (pH = 7.4): -0.91349983
• Log P: -0.913493
• Molar Refractivity: 83.781 cm^3
• Polarizability: 33.128002 Å^3
• Polar Surface Area: 128.84 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder
• Melting Point: 186°C

Product Information

• Purity: 97.5

DETAILS

Toronto Research Chemicals - C684400

A metabolite, and key biosynthetic intermediate for cell wall lignifcation within phenylpropanoid biosynthesis of coniferous trees. A substrate for Coniferin β-D-Glucosidase.

REFERENCES

• Hosokawa, A., et al.: Chem. Pharm. Bull., 52, 1265 (2004)
• Luo, B., et al.: Chem. Nat. Comp., 45, 371 (2004)
• She, G., et al.: Chem. & Biodivers., 6, 875 (2004)
• Liu, Q., et al.: J. Agric. Food Chem., 57, 586 (2004)