- 24513-41-51-Naphthalenecarboxylicacid,3,4,4a,5,6,7,8,8a-octahydro-5-[(3E)-5-methoxy-3-methyl-5-oxo-3-penten-1-yl]-5,6,8a-trimethyl-,(4aR,5S,6R,8aR)-
- 24513-51-75H-Cyclohepta[1,2-a:5,4-a']dinaphthalen-5-one,1,2,3,4,4a,7,7a,8,9,9a,10,11,12,13,13a,13b,14,15,15a,15b-eicosahydro-3,11-dihydroxy-4,4,7a,10,10,13a,15b-heptamethyl-,(3R,4aR,7aS,9aR,11R,13aR,13bS,15aS,15bR)- (9CI)
- 24513-57-31H-Cyclohepta[1,2-a:5,4-a']dinaphthalene-3,11-diol,2,3,4,4a,5,6,6a,7,9,9a,10,11,12,13,13a,13b,14,15,15a,15b-eicosahydro-4-(hydroxymethyl)-4,6a,10,10,13a,15b-hexamethyl-,(3S,4S,4aR,6aS,9aR,11R,13aR,13bS,15aS,15bR)- (9CI)
- 24515-49-9Naphthalene,2-(iodomethyl)-
- 2451-62-91,3,5-Triazine-2,4,6(1H,3H,5H)-trione,1,3,5-tris(2-oxiranylmethyl)-
- 24516-39-0Cholest-5-en-3-ol (3b)-, 3-(13Z)-13-docosenoate
- 24517-64-43-Pyridinecarbonitrile,2-amino-
- 2451-84-5Hexanedioic acid,1,6-bis(phenylmethyl) ester
- 24518-94-3Dispiro[2.2.2.2]decane
- 24519-27-51,4-Dithiin-2,3-dicarbonitrile,5,6-dihydro-
Hot Products
- 104987-11-3Tacrolimus
- 141-53-7Sodium formate
- 8001-54-5Quaternary ammonium compounds, alkylbenzyldimethyl, chlorides
- 9003-39-8Povidone
- 10161-34-9Trenbolone acetate
- 402957-28-2Telaprevir
- 68-19-9Cyanocobalamin
- 7631-86-9Silicon dioxide
- 302-79-4Tretinoin
- 77-92-9Citric acid
|
Basic Information |
|
Post buying leads |
|
Suppliers |
|
Cas Database |
| Name |
Geniposide |
EINECS | N/A |
| CAS No. | 24512-63-8 | Density | 1.59 g/cm3 |
| PSA | 155.14000 | LogP | -2.22910 |
| Solubility | N/A | Melting Point |
161-162 °C |
| Formula | C17H24O10 | Boiling Point | 693.7 °C at 760 mmHg |
| Molecular Weight | 388.372 | Flash Point | 251.3 °C |
| Transport Information | N/A | Appearance | N/A |
| Safety | 24/25 | Risk Codes | R36/37/38 |
| Molecular Structure |
|
Hazard Symbols |
 Xi
|
| 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; |
Article Data | 7 |
Geniposide Synthetic route
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 | Yield |
|---|---|
| With water In methanol for 1h; Ambient temperature; |
| Conditions | Yield |
|---|---|
| In methanol; hexane; chloroform at 20℃; for 1.5h; Inert atmosphere; | 18.4 mg |
- 24512-63-8
geniposide
| 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 | Yield |
|---|---|
| With sodium methylate In methanol at 50℃; for 3h; |
- 24512-63-8
geniposide
| 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 | 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 | 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
| 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 |
| 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% |
Geniposide Standards and Recommendations
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
Geniposide 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.](/UserFilesUpload/Uses of Geniposide(3).png)
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
What can I do for you?
Get Best Price
