Geniposide

• CAS: 24512-63-8
• Catalog Number: ACM24512638-1
• Category: Inhibitors
• Molecular Weight: 388.37
• Molecular Formula: C17H24O10
• Description: Geniposide is an iridoid glucoside extracted from Gardenia jasminoidesEllis fruits; exhibits a varity of biological activities such as anti-diabetic, antioxidative, antiproliferative and neuroprotective activities.
• Synonyms: 1α-(β-D-Glucopyranosyloxy)-1,4aα,5,7aα-tetrahydro-7-(hydroxymethyl)cyclopenta[c]pyran-4-carboxylic acid methyl ester
• IUPAC Name: Methyl (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• Canonical SMILES: COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C17H24O10/c1-24-15(23)9-6-25-16(11-7(4-18)2-3-8(9)11)27-17-14(22)13(21)12(20)10(5-19)26-17/h2,6,8,10-14,16-22H,3-5H2,1H3/t8-,10-,11-,12-,13+,14-,16+,17+/m1/s1
• InChI Key: IBFYXTRXDNAPMM-BVTMAQQCSA-N
• Boiling Point: 641.4±55.0 °C
• Melting Point: 160-164 °C
• Density: 1.54±0.1 g/ml
• Appearance: White powder
• Storage: Powder-20°C, 3 years; 4°C, 2 years; In solvent-80°C, 6 months; -20°C, 1 month.
• pKa: 12.80±0.70
• Shipping: Can be shipped at room temperature, where not in use may vary.
• Source: PlantsRubiaceaeGardenia jasminoides Ellis

Synthetic Use

Upstream Synthesis Route 1

• 27741-01-1
• 18107-18-1

• 24512-63-8

Reference: [1] Organic Letters, 2009, vol. 11, # 8, p. 1849 - 1851

Upstream Synthesis Route 2

• 1141938-70-6

• 24512-63-8

Reference: [1] Journal of Agricultural and Food Chemistry, 2018, vol. 66, # 6, p. 1341 - 1348

Upstream Synthesis Route 3

• 70094-79-0

• 24512-63-8

Reference: [1] Journal of Agricultural and Food Chemistry, 2018, vol. 66, # 6, p. 1341 - 1348

Upstream Synthesis Route 4

• 186581-53-3
• 27741-01-1

• 24512-63-8

Reference: [1]Chemical and Pharmaceutical Bulletin,1986,vol. 34,p. 4933 - 4938

Upstream Synthesis Route 5

• 27741-01-1
• 18107-18-1

• 24512-63-8

Reference: [1]Organic Letters,2009,vol. 11,p. 1849 - 1851

Downstream Synthesis Route 1

• 24512-63-8

• 27741-01-1

Reference: [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 3290 - 3296
[2]Patent: JP5753373,2015,B2 .Location in patent: Paragraph 0053
[3]Patent: CN110437291,2019,A .Location in patent: Paragraph 0020

* For details of the synthesis route, please refer to the original source to ensure accuracy.