27741-01-1

Basic information

• Product Name: Geniposidic acid
• Synonyms: (1S,4aS,7aS)-7-(hydroxymethyl)-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yloxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid;(1R,2S,6S)-9-(Hydroxymethyl)-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylic acid;GENIPOSIDIC ACID;Geniposidic acid std.;(1S)-1α-(β-D-Glucopyranosyloxy)-1,4aα,5,7aα-tetrahydro-7-hydroxymethylcyclopenta[c]pyran-4-carboxylic acid;(1S,4aS,7aS)-7-(Hydroxymethyl)-1-(β-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid;1α-(β-D-Glucopyranosyloxy)-1,4aα,5,7aα-tetrahydro-7-(hydroxymethyl)cyclopenta[c]pyran-4-carboxylic acid;GENIPOSIDIC ACID(SH)
• CAS NO: 27741-01-1
• Molecular Formula: C₁₆H₂₂O₁₀
• Molecular Weight: 374.34
• Product Categories: reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;Iridoids;chemical reagent;pharmaceutical intermediate;phytochemical
• Mol File: 27741-01-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 138-140 °C(Solv: methanol (67-56-1))
• Boiling Point: 684.1 °C at 760 mmHg
• Flash Point: 250.9 °C
• Appearance: /
• Density: 1.64 g/cm³
• Refractive Index: 1.659
• Storage Temp.: 2-8°C
• PKA: 4.49±0.60(Predicted)
• CAS DataBase Reference: Geniposidic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Geniposidic acid(27741-01-1)
• EPA Substance Registry System: Geniposidic acid(27741-01-1)

Safety Data

• Hazardous Substances Data: 27741-01-1(Hazardous Substances Data)

Usage

Uses

Geniposidic acid is an effective anticancer and radioprotection agent. Geniposidic acid might be a more potent tumor growth inhibitor than geniposide (GP) when combined with the X-irradiation, though there was no significant synergetic effect on their com

InChI:InChI=1/C16H22O10/c17-3-6-1-2-7-8(14(22)23)5-24-15(10(6)7)26-16-13(21)12(20)11(19)9(4-18)25-16/h1,5,7,9-13,15-21H,2-4H2,(H,22,23)/t7-,9-,10+,11-,12+,13-,15+,16+/m1/s1

Upstream product

• 24512-63-8 geniposide 
• 1141938-70-6 7-(2,2-dimethyl-propionyloxymethyl)-1-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester 
• 24512-63-8 geniposide 

Downstream Products

• 24512-63-8 geniposide 

Relevant articles and documents

Physicochemical, antimicrobial, and cytotoxic characteristics of a chitosan film cross-linked by a naturally occurring cross-linking agent, aglycone geniposidic acid

The purpose of this study was to evaluate the characteristics of a chitosan film cross-linked by a naturally occurring compound, aglycone geniposidic acid (aGSA). This newly developed aGSA-cross-linked chitosan film may be used as an edible film. The chitosan film without cross-linking (fresh) and the glutaraldehyde-cross-linked chitosan film were used as controls. The characteristics of test chitosan films evaluated were their degree of cross-linking, swelling ratio, mechanical properties, water vapor permeability, antimicrobial capability, cytotoxicity, and enzymatic degradability. It was found that cross-linking of chitosan films by aGSA (at a concentration up to 0.8 mM) significantly increased its ultimate tensile strength but reduced its strain at fracture and swelling ratio. There was no significant difference in the antimicrobial capability between the cross-linked chitosan films and their fresh counterpart. However, the aGSA-cross-linked chitosan film had a lower cytotoxicity, a slower degradation rate, and a relatively lower water vapor permeability as compared to the glutaraldehyde-cross-linked film. These results suggested that the aGSA-cross-linked chitosan film may be a promising material as an edible film.

Synthesis and biological evaluation of geniposide derivatives as potent and selective PTPlB inhibitors

Herein a series of Geniposide derivatives were designed, synthesized and evaluated as protein tyrosine phosphatase 1B (PTPlB) inhibitors. Most of these compounds exhibited potent in vitro PTP1B inhibitory activities, the representative 7a and 17f were found to be the most potent inhibitors against the enzyme with IC50 values of 0.35 and 0.41 μM, respectively. More importantly, they showcased 4 to10-fold selectivity over SHP2 and 3-fold over TCPTP. Further biological activity studies revealed that compounds 7a, 17b and 17f could effectively enhance insulin-stimulated glucose uptake with no significant cytotoxicity. Subsequent molecular docking and structural activity relationship analyses demonstrated that the glucose scaffold, benzylated glycosyl groups, and arylethenesulfonic acid ester significantly impact on the activity and selectivity.

The method of manufacturing a red dye and red dye bioactivation

PROBLEM TO BE SOLVED: To provide a manufacturing method for a red pigment having improved color tone. SOLUTION: The method for manufacturing the red pigment includes a step for reacting an iridoid compound having a carboxyl group at 4-position of an iridoid skeleton with an amino acid or a protein hydrolysate and a step for adding a compound for producing a sulfite ion to the reaction product. COPYRIGHT: (C)2012,JPO&INPIT