Geniposide supplier | CasNO.24512-63-8

Name
Geniposide
EINECS
CAS No. 24512-63-8
Article Data7
CAS DataBase
Density 1.59 g/cm³
Solubility
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
Appearance
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;
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%

: 24512-63-8
geniposide

: 116-11-0
2-Methoxypropene

: 77-76-9
2,2-dimethoxy-propane

A: 256221-80-4
4',6'-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide

B: 256221-82-6
2',3':4',6'-di-O-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide

Conditions

Conditions	Yield
Stage #1: geniposide; 2,2-dimethoxy-propane With pyridinium p-toluenesulfonate In acetone at 20 - 50℃; Substitution; Stage #2: 2-Methoxypropene In acetone at 20 - 50℃; Substitution;	A 55% B 22%

...Expand

: 24512-63-8
geniposide

: 76-83-5
trityl chloride

A: (1S,4aS,7aS)-7-Hydroxymethyl-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

B: 265096-97-7
(1S,4aS,7aS)-1-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-7-trityloxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
With pyridine at 20℃; tritylation;	A 14% B 37%

...Expand

: 24512-63-8
geniposide

A: 2280-44-6
D-Glucose

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

Conditions

Conditions	Yield
With β-glucosidase In water at 37℃; for 2h;

: 24512-63-8
geniposide

: (1S,4aS,7aS)-1-[(S)-2-Hydroxy-1-(2-hydroxy-1-hydroxymethyl-ethoxy)-ethoxy]-7-hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
With sodium tetrahydroborate; sodium periodate 1.) RT, 2 h, 2.) RT, 2 h; Multistep reaction;

: 24512-63-8
geniposide

: 52584-79-9
10-deoxygeniposide

Conditions

Conditions	Yield
With perchloric acid; hydrogen; palladium on activated charcoal In methanol	312.3 mg

: 24512-63-8
geniposide

: 108-24-7
acetic anhydride

: 49776-64-9
geniposide penta-acetate

Conditions

Conditions	Yield
In pyridine Ambient temperature;

: 24512-63-8
geniposide

: 100-52-7
benzaldehyde

: 78924-52-4
4',6'-O-benzylidene-geniposide

Conditions

Conditions	Yield
With zinc(II) chloride Ambient temperature;	26.26 g

: 24512-63-8
geniposide

A: C17H25(2)HO10

B: C17H25(2)HO10

Conditions

Conditions	Yield
With triethylamine; deuterium; palladium on activated charcoal Reduction; Title compound not separated from byproducts;

: 24512-63-8
geniposide

: 77-76-9
2,2-dimethoxy-propane

A: 4',6'-O-isopropylidene-geniposide

B: 2',3':4',6'-di-O-isopropylidene-geniposide

C: 256221-80-4
4',6'-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide

D: 10,6'-di-O-(1-methoxy-1-methylethyl)-geniposide

E 2',3':4',6'-di-O-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide: 2',3':4',6'-di-O-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In acetone at 20℃; for 36h; Substitution;	A n/a B 0.17 g C 8.08 g D 0.35 g E n/a

...Expand

: 24512-63-8
geniposide

: geniposidic acid aglucone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH / 1 h / 60 °C 2: cellulase / H2O / 18 h / 50 °C / pH 4.0 View Scheme

: 24512-63-8
geniposide

: 42830-28-4
(1S,4aS,7R,7aS)-7-Acetoxymethyl-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 37 percent / pyridine / 20 °C 2: 16.0 mg / pyridine 3: 76 percent / 80 percent aq. AcOH / 0.67 h / 80 °C 4: 50 percent / H2 / PtP2 / ethanol / 20 °C 5: 88 percent / pyridine View Scheme

: 24512-63-8
geniposide

: 42830-25-1
6,7-dihydroapodantheroside pentaacetate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 37 percent / pyridine / 20 °C 2: 16.0 mg / pyridine 3: 76 percent / 80 percent aq. AcOH / 0.67 h / 80 °C 4: 23 percent / H2 / PtP2 / ethanol / 20 °C 5: 80 percent / pyridine View Scheme

: 24512-63-8
geniposide

: 54621-24-8
(1S,4aS,7aS)-7-Hydroxymethyl-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 37 percent / pyridine / 20 °C 2: 16.0 mg / pyridine 3: 76 percent / 80 percent aq. AcOH / 0.67 h / 80 °C View Scheme

: 24512-63-8
geniposide

: 265097-02-7
(1S,4aS,7R,7aS)-7-Hydroxymethyl-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 37 percent / pyridine / 20 °C 2: 16.0 mg / pyridine 3: 76 percent / 80 percent aq. AcOH / 0.67 h / 80 °C 4: 50 percent / H2 / PtP2 / ethanol / 20 °C View Scheme

: 24512-63-8
geniposide

: 265097-01-6
(1S,4aS,7S,7aS)-7-Hydroxymethyl-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 37 percent / pyridine / 20 °C 2: 16.0 mg / pyridine 3: 76 percent / 80 percent aq. AcOH / 0.67 h / 80 °C 4: 23 percent / H2 / PtP2 / ethanol / 20 °C View Scheme

: 24512-63-8
geniposide

: 10-O-benzoyladoxoside tetraacetate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 37 percent / pyridine / 20 °C 2: 16.0 mg / pyridine 3: 76 percent / 80 percent aq. AcOH / 0.67 h / 80 °C 4: 23 percent / H2 / PtP2 / ethanol / 20 °C 5: 100 percent / pyridine / 20 °C View Scheme

: 24512-63-8
geniposide

: (1S,4aS,7aS)-7-Acetoxymethyl-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 14 percent / pyridine / 20 °C 2: pyridine View Scheme

: 24512-63-8
geniposide

: 265096-99-9
(1S,4aS,7aS)-1-((2S,3R,4S,5R,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-7-trityloxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 37 percent / pyridine / 20 °C 2: 16.0 mg / pyridine View Scheme

: 24512-63-8
geniposide

: 42830-26-2
6,7-dihydroapodantheroside

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C 2.1: Et3N; H2 / Pd/C / ethanol / 4.5 h 2.2: 69 percent / aq. HOAc / 3 h / 45 - 50 °C View Scheme

: 24512-63-8
geniposide

: 256221-89-3
(4S,4aS,7S,7aR)-4-Hydroxy-7-hydroxymethyl-hexahydro-cyclopenta[c]pyran-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C View Scheme

: 24512-63-8
geniposide

: 256221-90-6
(S)-1-((1S,2R,3S)-2,3-Bis-hydroxymethyl-cyclopentyl)-ethane-1,2-diol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C 3: 93 percent / NaBH4 / ethanol / 2.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C 2.1: Et3N; H2 / Pd/C / ethanol / 4.5 h 2.2: 69 percent / aq. HOAc / 3 h / 45 - 50 °C 3.1: O3 / CH2Cl2; methanol / 0.5 h / -78 °C 3.2: 70 percent / NaBH4 / CH2Cl2; methanol; ethanol / -78 - 20 °C View Scheme

: 24512-63-8
geniposide

: 256221-91-7
[(1R,2S,5S)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-hydroxymethyl-cyclopentyl]-methanol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C 3: 93 percent / NaBH4 / ethanol / 2.5 h / 20 °C 4: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h View Scheme
Multi-step reaction with 3 steps 1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C 3: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h View Scheme
Multi-step reaction with 4 steps 1.1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C 2.1: Et3N; H2 / Pd/C / ethanol / 4.5 h 2.2: 69 percent / aq. HOAc / 3 h / 45 - 50 °C 3.1: O3 / CH2Cl2; methanol / 0.5 h / -78 °C 3.2: 70 percent / NaBH4 / CH2Cl2; methanol; ethanol / -78 - 20 °C 4.1: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h View Scheme

: 24512-63-8
geniposide

: [(1S,2R,5S)-2-(6-Amino-purin-9-ylmethyl)-5-hydroxymethyl-cyclopentyl]-methanol

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C 3.1: 93 percent / NaBH4 / ethanol / 2.5 h / 20 °C 4.1: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h 5.1: NaH / tetrahydrofuran / 0 - 20 °C 5.2: Bu4NI / tetrahydrofuran / 20 °C 6.1: 1.86 g / aq. HCl / tetrahydrofuran / 24 h / 20 °C 7.1: H5IO6 / tetrahydrofuran / 0.25 h / 20 °C 7.2: K2CO3 / methanol / 4 h / 20 °C 7.3: 94 percent / NaBH4 / methanol / 16 h 8.1: 68.5 percent / Ph3P; DEAD / dioxane / 19 h / 20 °C 9.1: 97 percent / BCl3 / CH2Cl2 / -78 - -25 °C View Scheme
Multi-step reaction with 9 steps 1.1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C 2.1: Et3N; H2 / Pd/C / ethanol / 4.5 h 2.2: 69 percent / aq. HOAc / 3 h / 45 - 50 °C 3.1: O3 / CH2Cl2; methanol / 0.5 h / -78 °C 3.2: 70 percent / NaBH4 / CH2Cl2; methanol; ethanol / -78 - 20 °C 4.1: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h 5.1: NaH / tetrahydrofuran / 0 - 20 °C 5.2: Bu4NI / tetrahydrofuran / 20 °C 6.1: 1.86 g / aq. HCl / tetrahydrofuran / 24 h / 20 °C 7.1: H5IO6 / tetrahydrofuran / 0.25 h / 20 °C 7.2: K2CO3 / methanol / 4 h / 20 °C 7.3: 94 percent / NaBH4 / methanol / 16 h 8.1: 68.5 percent / Ph3P; DEAD / dioxane / 19 h / 20 °C 9.1: 97 percent / BCl3 / CH2Cl2 / -78 - -25 °C View Scheme

Yield

Multi-step reaction with 9 steps
1.1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C
3.1: 93 percent / NaBH4 / ethanol / 2.5 h / 20 °C
4.1: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h
5.1: NaH / tetrahydrofuran / 0 - 20 °C
5.2: Bu4NI / tetrahydrofuran / 20 °C
6.1: 1.86 g / aq. HCl / tetrahydrofuran / 24 h / 20 °C
7.1: H5IO6 / tetrahydrofuran / 0.25 h / 20 °C
7.2: K2CO3 / methanol / 4 h / 20 °C
7.3: 94 percent / NaBH4 / methanol / 16 h
8.1: 68.5 percent / Ph3P; DEAD / dioxane / 19 h / 20 °C
9.1: 97 percent / BCl3 / CH2Cl2 / -78 - -25 °C
View Scheme

Multi-step reaction with 9 steps
1.1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C
2.1: Et3N; H2 / Pd/C / ethanol / 4.5 h
2.2: 69 percent / aq. HOAc / 3 h / 45 - 50 °C
3.1: O3 / CH2Cl2; methanol / 0.5 h / -78 °C
3.2: 70 percent / NaBH4 / CH2Cl2; methanol; ethanol / -78 - 20 °C
4.1: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h
5.1: NaH / tetrahydrofuran / 0 - 20 °C
5.2: Bu4NI / tetrahydrofuran / 20 °C
6.1: 1.86 g / aq. HCl / tetrahydrofuran / 24 h / 20 °C
7.1: H5IO6 / tetrahydrofuran / 0.25 h / 20 °C
7.2: K2CO3 / methanol / 4 h / 20 °C
7.3: 94 percent / NaBH4 / methanol / 16 h
8.1: 68.5 percent / Ph3P; DEAD / dioxane / 19 h / 20 °C
9.1: 97 percent / BCl3 / CH2Cl2 / -78 - -25 °C
View Scheme

: 24512-63-8
geniposide

: [(1S,2S,5S)-2-(6-Amino-purin-9-ylmethyl)-5-hydroxymethyl-cyclopentyl]-methanol

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C 3: 93 percent / NaBH4 / ethanol / 2.5 h / 20 °C 4: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h 5: pyridine / CH2Cl2 / 4 - 20 °C 6: 1.47 g / aq. HCl / tetrahydrofuran / 34 h / 20 °C 7: H5IO6 / tetrahydrofuran / 0.5 h / 20 °C 8: 0.48 g / NaBH4 / CH2Cl2; ethanol / -78 - 20 °C 9: Ph3P; DEAD / tetrahydrofuran / 12 h / 20 °C 10: 35 percent / liq. NH3 / 72 h / 45 - 50 °C View Scheme
Multi-step reaction with 10 steps 1.1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C 2.1: Et3N; H2 / Pd/C / ethanol / 4.5 h 2.2: 69 percent / aq. HOAc / 3 h / 45 - 50 °C 3.1: O3 / CH2Cl2; methanol / 0.5 h / -78 °C 3.2: 70 percent / NaBH4 / CH2Cl2; methanol; ethanol / -78 - 20 °C 4.1: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h 5.1: pyridine / CH2Cl2 / 4 - 20 °C 6.1: 1.47 g / aq. HCl / tetrahydrofuran / 34 h / 20 °C 7.1: H5IO6 / tetrahydrofuran / 0.5 h / 20 °C 8.1: 0.48 g / NaBH4 / CH2Cl2; ethanol / -78 - 20 °C 9.1: Ph3P; DEAD / tetrahydrofuran / 12 h / 20 °C 10.1: 35 percent / liq. NH3 / 72 h / 45 - 50 °C View Scheme

Yield

Multi-step reaction with 10 steps
1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C
3: 93 percent / NaBH4 / ethanol / 2.5 h / 20 °C
4: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h
5: pyridine / CH2Cl2 / 4 - 20 °C
6: 1.47 g / aq. HCl / tetrahydrofuran / 34 h / 20 °C
7: H5IO6 / tetrahydrofuran / 0.5 h / 20 °C
8: 0.48 g / NaBH4 / CH2Cl2; ethanol / -78 - 20 °C
9: Ph3P; DEAD / tetrahydrofuran / 12 h / 20 °C
10: 35 percent / liq. NH3 / 72 h / 45 - 50 °C
View Scheme

Multi-step reaction with 10 steps
1.1: 8.08 g / pyridinium p-toluenesulfonate / acetone / 36 h / 20 °C
2.1: Et3N; H2 / Pd/C / ethanol / 4.5 h
2.2: 69 percent / aq. HOAc / 3 h / 45 - 50 °C
3.1: O3 / CH2Cl2; methanol / 0.5 h / -78 °C
3.2: 70 percent / NaBH4 / CH2Cl2; methanol; ethanol / -78 - 20 °C
4.1: 81 percent / pyridinium p-toluenesulfonate; CuSO4 / acetone / 6 h
5.1: pyridine / CH2Cl2 / 4 - 20 °C
6.1: 1.47 g / aq. HCl / tetrahydrofuran / 34 h / 20 °C
7.1: H5IO6 / tetrahydrofuran / 0.5 h / 20 °C
8.1: 0.48 g / NaBH4 / CH2Cl2; ethanol / -78 - 20 °C
9.1: Ph3P; DEAD / tetrahydrofuran / 12 h / 20 °C
10.1: 35 percent / liq. NH3 / 72 h / 45 - 50 °C
View Scheme

Geniposide 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

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.

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

Product Name

Geniposide

Synthetic route

Geniposide Standards and Recommendations

Geniposide Specification

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