24512-63-8

Basic information

• Product Name: Geniposide
• Synonyms: GENIPOSIDE;Methyl (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-carboxylate;glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-,methyl ester, (1S,4aS,7aS)-;(1S)-1α-(β-D-Glucopyranosyloxy)-1,4aα,5,7aα-tetrahydro-7-hydroxymethylcyclopenta[c]pyran-4-carboxylic acid methyl ester;1α-(β-D-Glucopyranosyloxy)-1,4aα,5,7aα-tetrahydro-7-(hydroxymethyl)cyclopenta[c]pyran-4-carboxylic acid methyl ester;Geniposide ,98%;Olea europaea L;Geniposidic
• CAS NO: 24512-63-8
• Molecular Formula: C₁₇H₂₄O₁₀
• Molecular Weight: 388.37
• Product Categories: Iridoids;Standard extract;Natural Plant Extract;Glucagon receptor and related;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 24512-63-8.mol

Chemical Properties

• Melting Point: 160.0 to 164.0 °C
• Boiling Point: 693.7 °C at 760 mmHg
• Flash Point: 251.3 °C
• Appearance: white to beige/
• Density: 1.59 g/cm³
• Storage Temp.: ?20°C
• Solubility: H2O: ≥5mg/mL
• PKA: 12.80±0.70(Predicted)
• CAS DataBase Reference: Geniposide(CAS DataBase Reference)
• NIST Chemistry Reference: Geniposide(24512-63-8)
• EPA Substance Registry System: Geniposide(24512-63-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 24512-63-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Geniposide is used as a key ingredient in multi-component injections for the treatment of cerebrovascular diseases. It is valued for its ability to improve blood circulation and provide neuroprotective effects, making it a crucial component in managing and treating such conditions.
Used in Traditional Medicine:
Geniposide is also utilized in traditional medicine, particularly in Chinese medicine, where it is known for its detoxifying and anti-inflammatory properties. It is often used to treat conditions such as jaundice and inflammation.
Used in Drug Development:
Due to its various biological activities, Geniposide is a promising candidate for drug development. Researchers are exploring its potential in developing new medications for a range of health conditions, including neurological disorders and inflammatory diseases.

Pharmacological effects

Geniposide, also known as Gardenia glycosides, geniposide. It is a brown to white crystalline powder, with little flavor and no bitter taste, a cycloolefin ether glycoside compound extracted from the dry and ripe fruit of Rubiaceae Gardenia. Geniposide has a significant role in promoting bile secretion, and can reduce blood bilirubin, as well as promote rapid excretion of bilirubin in the blood. It has an inhibitory effect on Streptococcus hemolyticus and skin fungi. It also has antipyretic, analgesic, sedative, antihypertensive and hemostatic effects. Geniposide has the function of purging pathogenic fire and eliminating restlessness, clearing heat and eliminating damp, decreasing swellinging to relieving pain. The Indications of Geniposide are heat disease, dysphoria, coma delirium, jaundice, heat stranguria, heat in blood, swelling and pain of eye, pathopyretic ulcer, and sprain.

Biochem/physiol Actions

Geniposide is an iridoid glycoside with a variety of biological activities including neuroprotective, anti-diabetic, antiproliferative, and antioxidative activity. Geniposide has been shown to regulate Nrf2 translocation and upregulate downstream antioxidant protein HO-1 expression through the PI3K/Akt signaling pathway, which may account for its neuroprotective and antioxidative activity. Glucagon-like peptide 1 (GLP-1) receptor may also play a critical role in geniposide induced HO-1 expression.

Synthetic route

diazomethane (186581-53-3, 908094-01-9) + geniposidic acid (27741-01-1) → geniposide (24512-63-8)

10-O-(5-phenyl-2,4-pentadienoyl)-geniposide → geniposide (24512-63-8) + (2E,4E)-methyl 5-phenylpenta-2,4-dienoate (38447-05-1, 38448-84-9, 101934-35-4, 121411-05-0, 1516-24-1, 24196-39-2)

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

geniposidic acid (27741-01-1) + diazomethyl-trimethyl-silane (18107-18-1) → geniposide (24512-63-8)

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 → geniposide (24512-63-8)

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

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 (1141938-70-6) → geniposide (24512-63-8)

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

genipin (70094-79-0, 73610-59-0, 6902-77-8) → geniposide (24512-63-8)

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

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 (861695-58-1) + geniposide (24512-63-8) → C43H67NO30 (1093135-91-1)

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%

geniposide (24512-63-8) → geniposidic acid (27741-01-1)

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;

geniposide (24512-63-8) → genipin (70094-79-0, 73610-59-0, 6902-77-8)

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

geniposide (24512-63-8) + benzyl bromide (100-39-0) → 7-benzyl-1-(3,4,5,6-tetrabenzyl)geniposide

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 (24512-63-8) + 2-Methoxypropene (116-11-0) + 2,2-dimethoxy-propane (77-76-9) → 4',6'-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide (256221-80-4) + 2',3':4',6'-di-O-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide (256221-82-6)

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%

geniposide (24512-63-8) + trityl chloride (76-83-5) → (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 + (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 (265096-97-7)

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

geniposide (24512-63-8) → D-Glucose (2280-44-6) + genipin (70094-79-0, 73610-59-0, 6902-77-8)

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

geniposide (24512-63-8) → (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	Yield
With sodium tetrahydroborate; sodium periodate 1.) RT, 2 h, 2.) RT, 2 h; Multistep reaction;

geniposide (24512-63-8) → 10-deoxygeniposide (52584-79-9)

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

geniposide (24512-63-8) + acetic anhydride (108-24-7) → geniposide penta-acetate (49776-64-9)

Conditions	Yield
In pyridine Ambient temperature;

geniposide (24512-63-8) + benzaldehyde (100-52-7) → 4',6'-O-benzylidene-geniposide (78924-52-4)

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

geniposide (24512-63-8) → C17H25(2)HO10 + C17H25(2)HO10

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

geniposide (24512-63-8) + 2,2-dimethoxy-propane (77-76-9) → 4',6'-O-isopropylidene-geniposide + 2',3':4',6'-di-O-isopropylidene-geniposide + 4',6'-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide (256221-80-4) + 10,6'-di-O-(1-methoxy-1-methylethyl)-geniposide + 2',3':4',6'-di-O-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide

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

geniposide (24512-63-8) → geniposidic acid aglucone

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

geniposide (24512-63-8) → (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 (42830-28-4)

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

geniposide (24512-63-8) → 6,7-dihydroapodantheroside pentaacetate (42830-25-1)

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

geniposide (24512-63-8) → (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 (54621-24-8)

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

geniposide (24512-63-8) → (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 (265097-02-7)

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

geniposide (24512-63-8) → (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 (265097-01-6)

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

geniposide (24512-63-8) → 10-O-benzoyladoxoside tetraacetate

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

geniposide (24512-63-8) → (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	Yield
Multi-step reaction with 2 steps 1: 14 percent / pyridine / 20 °C 2: pyridine View Scheme

geniposide (24512-63-8) → (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 (265096-99-9)

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

geniposide (24512-63-8) → 6,7-dihydroapodantheroside (42830-26-2)

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

geniposide (24512-63-8) → (4S,4aS,7S,7aR)-4-Hydroxy-7-hydroxymethyl-hexahydro-cyclopenta[c]pyran-3-one (256221-89-3)

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

geniposide (24512-63-8) → (S)-1-((1S,2R,3S)-2,3-Bis-hydroxymethyl-cyclopentyl)-ethane-1,2-diol (256221-90-6)

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

geniposide (24512-63-8) → [(1R,2S,5S)-2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-hydroxymethyl-cyclopentyl]-methanol (256221-91-7)

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

geniposide (24512-63-8) → [(1S,2R,5S)-2-(6-Amino-purin-9-ylmethyl)-5-hydroxymethyl-cyclopentyl]-methanol

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

geniposide (24512-63-8) → [(1S,2S,5S)-2-(6-Amino-purin-9-ylmethyl)-5-hydroxymethyl-cyclopentyl]-methanol

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

Upstream product

• 186581-53-3 diazomethane 
• 27741-01-1 geniposidic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 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 
• 70094-79-0 genipin 

Downstream Products

• 2280-44-6 D-Glucose 
• 70094-79-0 genipin 
• 49776-64-9 geniposide penta-acetate 
• 78924-52-4 4',6'-O-benzylidene-geniposide 
• 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 
• 27741-01-1 geniposidic acid 
• 78924-59-1 (2aR,3S,4aS,7aS,7bS)-3-(Toluene-4-sulfonyloxy)-2a,3,4,4a,7a,7b-hexahydro-2H-1,7-dioxa-cyclopenta[cd]indene-5-carboxylic acid methyl ester 
• 78924-53-5 4',6'-O-benzylidene-2',3',10-tri-O-benzyl-geniposide 
• 78924-60-4 (1S,4aS,7R,7aS)-7-Benzyloxymethyl-1-((2R,4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-1,4a,7,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester 
• 78924-60-4 (1S,4aS,7S,7aS)-7-Benzyloxymethyl-1-((2R,4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-1,4a,7,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester 
• 78924-54-6 4',6'-O-benzylidene-2',3',10-tri-O-benzyl-7-epi-allo-10-hydroxyloganin 
• 78924-54-6 4',6'-O-benzylidene-2',3',10-tri-O-benzyl-allo-10-hydroxyloganin 
• 78924-54-6 4',6'-O-benzylidene-2',3',10-tri-O-benzyl-7-epi-10-hydroxyloganin 
• 78924-54-6 4',6'-O-benzylidene-2',3',10-tri-O-benzyl-10-hydroxyloganin 

Relevant articles and documents

Discovery of Glycosylated Genipin Derivatives as Novel Antiviral, Insecticidal, and Fungicidal Agents

A series of novel genipin glycoside derivatives incorporating 11 glycosidic moieties at either the 1 or 10 position of genipin were designed and synthesized. These compounds exhibited moderate to excellent inhibitory activities against tobacco mosaic virus. Especially, the in vitro and in vivo activities of compounds 6e, 7c, 7d, 7f, 7h, and 7i were comparable to that of ribavirin. In particular, compound 7c, the mannosyl derivative of genipin at the 10 position, showed the best activity. The series of genipin glycosyl derivatives also displayed fungicidal activities against 14 kinds of phytopathogenic fungi, especially for Rhizoctonia cerealis and Sclerotinia sclerotiorum. Moreover, compound 6h exhibited good insecticidal activity against diamondback moth; compounds 7b, 7c, and 7g exhibited moderate insecticidal activity against three kinds of Lepidoptera pests (oriental armyworm, cotton bollworm, and corn borer); and compound 7e showed excellent larvacidal activities against mosquito.

Asymmetric total synthesis of the iridoid β-glucoside (+)-geniposide via phosphine organocatalysis

Phosphine-catalyzed [3 + 2] cycloaddition of ethyl-2, 3-butadienoate with enone (S)-3b occurs with high levels of regio- and stereocontrol to deliver the c/s-fused cyclopenta[c]pyran 4 characteristic of the iridoid family of natural products. Cycloadduct 4 was converted to the iridoid glycoside (+)-geniposide in 10 steps.

Hair dyeing by iridoid glycosides and aglycons thereof

A method of dyeing hair which comprises contacting hair with an iridoid glycoside or an aglycon thereof.

IRIDOID GLUCOSIDES IN AVICENNIA MARINA

Key Word Index - Avicennia marina; Verbenaceae; iridoids; geniposidic acid; mussaenosidic acid; 2'-cinnamoylmussaenosidic acid; 10-O-(5-phenyl-2,4-pentadienoyl)-geniposidic acid; 7-O-(5-phenyl-2,4-pentadienoyl)-8-epiloganic acid. - 2'-Cinnamoyl-mussaenoside , 10-O-(5-phenyl-2,4-pentadienoyl)-geniposide, 7-O-(5-phenyl-2,4-pentadienoyl)-8-epiloganin, and the known iridoids geniposide and mussaenoside have been isolated from a methylated extract of the leaves of Avicennia marina.Evidence is presented that the iridoids occur as the free acids in the plant.The taxonomic significance of these findings is discussed.

Red coloring composite and the method for its production

PCT No. PCT/JP78/00054 PCT Filed Dec. 14, 1978 Sec. 371 Date Aug. 9, 1979 Sec. 102(e) Date Aug. 9, 1979 PCT Pub. No. WO79/00394 PCT Pub. Date Jul. 12, 1979. Novel reddish coloring compounds of varying hue and the method for its production, obtained by reaction between iridoid compounds contained in biological substances, where if necessary, by pretreatment with chemical or enzymic means to form --COOH at the C-4 position, and in the case of glycosides by hydrolysis of iridoid compounds to aglycones with chemical or microbial or enzymic means, and a substance possessing a primary amino group under acidic condition.