Name: Geniposide
SKU: 24512-63-8

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Basic Information

Molecular Structure:
CAS No.:	24512-63-8
Name:	Geniposide

Formula:	C₁₇H₂₄O₁₀
Molecular Weight:	388.372
Synonyms:	Cyclopenta[c]pyran-4-carboxylicacid, 1-(b-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-,methyl ester, [1S-(1a,4aa,7aa)]-;Geniposide(8CI);Cyclopenta(c)pyran-4-carboxylic acid, 1-(beta-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-, methyl ester, (1S-(1alpha,4aalpha,7aalpha))-;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;(1S,4aS,7aS)-4-(Hydroxyacetyl)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl D-glucopyranoside;
Density:	1.59 g/cm³
Melting Point:	161-162 °C
Boiling Point:	693.7 °C at 760 mmHg
Flash Point:	251.3 °C
Hazard Symbols:	Xi
Risk Codes:	R36/37/38
Safety:	24/25
PSA:	155.14000
LogP:	-2.22910

Synthetic route

: 186581-53-3, 908094-01-9
diazomethane

: 27741-01-1
geniposidic acid

: 24512-63-8
geniposide

: 10-O-(5-phenyl-2,4-pentadienoyl)-geniposide

A: 24512-63-8
geniposide

B: 38447-05-1, 38448-84-9, 101934-35-4, 121411-05-0, 1516-24-1, 24196-39-2
(2E,4E)-methyl 5-phenylpenta-2,4-dienoate

Conditions

Conditions	Yield
With water In methanol for 1h; Ambient temperature;

: 27741-01-1
geniposidic acid

: 18107-18-1
diazomethyl-trimethyl-silane

: 24512-63-8
geniposide

Conditions

Conditions	Yield
In methanol; hexane; chloroform at 20℃; for 1.5h; Inert atmosphere;	18.4 mg

: methyl (1R,4aS,7aS)-1-Hydroxy-7-((pivaloyloxy)-methyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

: 24512-63-8
geniposide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3.5 h / -30 - 20 °C / Molecular sieve; Inert atmosphere 2: sodium methylate / methanol / 3 h / 50 °C View Scheme

: 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

Conditions

Conditions	Yield
With sodium methylate In methanol at 50℃; for 3h;

: 70094-79-0, 73610-59-0, 6902-77-8
genipin

: 24512-63-8
geniposide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere 2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3.5 h / -30 - 20 °C / Molecular sieve; Inert atmosphere 3: sodium methylate / methanol / 3 h / 50 °C View Scheme

: 861695-58-1
O-[(α-D-mannopyranosyl)-(1->6)-(α-D-mannopyranosyl)-(1->3)-β-D-mannopyranosyl]-(1->4)-(1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-methyloxazoline

: 24512-63-8
geniposide

: 1093135-91-1
C43H67NO30

Conditions

Conditions	Yield
With endo-β-N-acetylglucosaminidase from Arthrobactor protophormiae In dimethyl sulfoxide at 23℃; for 2h; pH=7.0; aq. phosphate buffer; Enzymatic reaction;	100%

: 24512-63-8
geniposide

: 27741-01-1
geniposidic acid

Conditions

Conditions	Yield
With lithium hydroxide In methanol at 50℃;	90%
With sodium hydroxide at 60℃; for 1h;
With water; sodium hydroxide at 60℃; for 1.5h; Concentration;
With sodium hydroxide at 60℃; for 2h;

: 24512-63-8
geniposide

: 70094-79-0, 73610-59-0, 6902-77-8
genipin

Conditions

Conditions	Yield
With water In dichloromethane at 37℃; for 24h; Enzymatic reaction;	84%
With immobilized β-glucosidase In ethyl acetate at 55℃; pH=4.5; aq. acetate buffer;	63.08%
With acetate buffer; β-glucosidase at 37℃; for 5h; pH=5.0;	0.5 g

: 24512-63-8
geniposide

: 100-39-0
benzyl bromide

: 7-benzyl-1-(3,4,5,6-tetrabenzyl)geniposide

Conditions

Conditions	Yield
Stage #1: geniposide With sodium hydride In N,N-dimethyl-formamide; mineral oil for 1h; Cooling with ice; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃;	70%
Stage #1: geniposide With sodium hydride In N,N-dimethyl-formamide for 1h; Cooling with ice; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃;	42%
Stage #1: geniposide With sodium hydride In N,N-dimethyl-formamide for 1h; Cooling with ice; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃;	42%

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Standards and Recommendations

Geniposide's health indicators
The number of colonies:GB/4789.2-1994
Coliforms:GB/4789.3-1994
Mold and yeast:GB/4789.15-1994
Pathogens:GB4789.4～5、10～11

Specification

The Geniposide with CAS registry number of 24512-63-8 is also known as (1S,4aS,7aS)-4-(Hydroxyacetyl)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl D-glucopyranoside. The IUPAC name is 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. It belongs to product categories of Iridoids; Standard extract; Natural Plant Extract; Glucagon Receptor and Related. In addition, the formula is C₁₇H₂₄O₁₀ and the molecular weight is 388.37.

Physical properties about Geniposide are: (1)# of Rule of 5 Violations: 2 ; (2)#H bond acceptors: 10; (3)#H bond donors: 6; (4)#Freely Rotating Bonds: 12; (5)Polar Surface Area: 166.14Å²; (6)Index of Refraction: 1.647; (7)Molar Refractivity: 88.37 cm³; (8)Molar Volume: 243.1 cm³; (9)Surface Tension: 86.8 dyne/cm; (10)Density: 1.59 g/cm³; (11)Flash Point: 251.3 °C; (12)Enthalpy of Vaporization: 116.2 kJ/mol; (13)Boiling Point: 693.7 °C at 760 mmHg; (14)Vapour Pressure: 2.91E-22 mmHg at 25 °C.

Uses of Geniposide: it is used to produce 7-hydroxymethyl-1-(3,4,5-trihydroxy-6-tritylox and trityloxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester by reaction with chloro-triphenyl-methane. The reaction occurs with reagent pyridine at 20 °C. The yield is about 37%.

Geniposide is used to produce 7-hydroxymethyl-1-(3,4,5-trihydroxy-6-tritylox and trityloxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester by reaction with chloro-triphenyl-methane.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: COC(=O)C1=COC(C2C1CC=C2CO)OC3C(C(C(C(O3)CO)O)O)O
2. Isomeric 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
3. 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
4. InChIKey: IBFYXTRXDNAPMM-BVTMAQQCSA-N

24512-63-8

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Standards and Recommendations

Specification