24512-62-7

Basic information

• Product Name: GARDENOSIDE
• Synonyms: GARDENOSIDE;GARDENOSIDE hplc;Cyclopenta[c]pyran-4-carboxylicacid, 1-(β-D-;glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-,methyl ester, (1S,4aS,7S,7aS)-;(1S)-1α-(β-D-Glucopyranosyloxy)-1,4aα,7,7aα-tetrahydro-7α-hydroxy-7-hydroxymethylcyclopenta[c]pyran-4-carboxylic acid methyl ester;1α-(β-D-Glucopyranosyloxy)-1,4aα,7,7aα-tetrahydro-7α-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-4-carboxylic acid methyl ester;GARDENOSIDE(RG);Gardenoside, 98%, from Gardenia jasminoides J. Ellis
• CAS NO: 24512-62-7
• Molecular Formula: C₁₇H₂₄O₁₁
• Molecular Weight: 404.37
• Product Categories: Iridoids;API
• Mol File: 24512-62-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 118～120℃
• Boiling Point: 672.8 °C at 760 mmHg
• Flash Point: 242.1 °C
• Appearance: Powder.
• Density: 1.61 g/cm³
• Vapor Pressure: 5.53E-21mmHg at 25°C
• Refractive Index: 1.643
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.28±0.60(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: GARDENOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: GARDENOSIDE(24512-62-7)
• EPA Substance Registry System: GARDENOSIDE(24512-62-7)

Safety Data

• Hazardous Substances Data: 24512-62-7(Hazardous Substances Data)

Usage

Description

GARDENOSIDE, a cyclopentapyran derivative, is a plant extract with significant medicinal properties. It is characterized by the presence of hydroxy and hydroxymethyl groups at position 7, replacing the methyl and hydrogen groups found in 7-deoxyloganin. GARDENOSIDE is widely recognized for its therapeutic applications in traditional Chinese medicine and has demonstrated potential in various health-related areas.

Uses

Used in Traditional Chinese Medicine:
GARDENOSIDE is used as an anti-viral agent in traditional Chinese medicine, where it serves as a key component of anti-viral medicines. Its natural origin and potential to combat viral infections make it a valuable addition to the medicinal repertoire.
Used in Antidepressant Applications:
GARDENOSIDE is also used as an anti-depression medication, being a component of the Zhi-zi-chi decoction. This traditional remedy is known for its mood-enhancing and stress-relieving properties, contributing to the overall well-being of individuals suffering from depressive disorders.

InChI:InChI=1/C17H24O11/c1-25-14(23)8-5-26-15(10-7(8)2-3-17(10,24)6-19)28-16-13(22)12(21)11(20)9(4-18)27-16/h2-3,5,7,9-13,15-16,18-22,24H,4,6H2,1H3/t7-,9-,10-,11-,12+,13-,15+,16+,17-/m1/s1

Synthetic route

10-dehydrogardenoside (82345-51-5) → gardenoside (24512-62-7)

Conditions	Yield
With sodium tetrahydroborate In ethanol for 1h; Ambient temperature;

gardenoside (24512-62-7) → randioside

Conditions	Yield
With sodium periodate In phosphate buffer at 20℃; for 0.25h; pH=6.0; Oxidation;	73%

gardenoside (24512-62-7) → D-Glucose (2280-44-6) + (2aS,4aS,5S,7aR,7bS)-2a,6,7a-Trihydroxy-2a,4a,5,6,7a,7b-hexahydro-2H-1,7-dioxa-cyclopenta[cd]indene-5-carboxylic acid methyl ester (104538-06-9)

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

gardenoside (24512-62-7) → 6-deoxyretzioside

Conditions

Yield

Multi-step reaction with 10 steps 1: 73 percent / NaIO4 / aq. phosphate buffer / 0.25 h / 20 °C / pH 6.0 2: 88 percent / pyridine / 0.25 h 3: 94 percent / NaBH4 / methanol / 0.08 h 4: 57 percent / aq. NaOH; (n-Bu)4NHSO4 / toluene / 3 h / 20 °C 5: quinoline / 1.5 h / 200 °C 6: AcOH / methanol / 17 h 7: 120 mg / aq. NaOH / 3.5 h 8: 92 percent / pyridine / 2 h 9: 150 mg / CuCO3*Cu(OH)2 / quinoline / 2 h / 200 °C 10: 13 mg / MeONa / methanol / 2 h / 20 °C View Scheme

gardenoside (24512-62-7) → [6β,8-2H2]-6-deoxyretzioside

Conditions

Yield

Multi-step reaction with 10 steps 1: 73 percent / NaIO4 / aq. phosphate buffer / 0.25 h / 20 °C / pH 6.0 2: 88 percent / pyridine / 0.25 h 3: NaBD4 / methanol 4: 47 percent / aq. NaOH; (n-Bu)4NHSO4 / toluene / 3 h / 20 °C 5: quinoline / 1.5 h / 200 °C 6: AcOH / methanol 7: 160 mg / aq. NaOH 8: 92 percent / pyridine / 2 h 9: 163 mg / CuCO3*Cu(OH)2 / quinoline / 2 h / 200 °C 10: 37 mg / MeONa / methanol / 2 h / 20 °C View Scheme

gardenoside (24512-62-7) → (1S,4aS,7aR)-1-((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions	Yield
Multi-step reaction with 6 steps 1: 73 percent / NaIO4 / aq. phosphate buffer / 0.25 h / 20 °C / pH 6.0 2: 88 percent / pyridine / 0.25 h 3: 94 percent / NaBH4 / methanol / 0.08 h 4: 57 percent / aq. NaOH; (n-Bu)4NHSO4 / toluene / 3 h / 20 °C 5: quinoline / 1.5 h / 200 °C 6: AcOH / methanol / 17 h View Scheme

gardenoside (24512-62-7) → 10-nor-geniposidic acid

Conditions	Yield
Multi-step reaction with 7 steps 1: 73 percent / NaIO4 / aq. phosphate buffer / 0.25 h / 20 °C / pH 6.0 2: 88 percent / pyridine / 0.25 h 3: 94 percent / NaBH4 / methanol / 0.08 h 4: 57 percent / aq. NaOH; (n-Bu)4NHSO4 / toluene / 3 h / 20 °C 5: quinoline / 1.5 h / 200 °C 6: AcOH / methanol / 17 h 7: 120 mg / aq. NaOH / 3.5 h View Scheme

gardenoside (24512-62-7) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(1S,4aR,7aR)-(1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-1-yl)oxy]-tetrahydro-pyran-3-yl ester

Conditions

Yield

Multi-step reaction with 9 steps 1: 73 percent / NaIO4 / aq. phosphate buffer / 0.25 h / 20 °C / pH 6.0 2: 88 percent / pyridine / 0.25 h 3: 94 percent / NaBH4 / methanol / 0.08 h 4: 57 percent / aq. NaOH; (n-Bu)4NHSO4 / toluene / 3 h / 20 °C 5: quinoline / 1.5 h / 200 °C 6: AcOH / methanol / 17 h 7: 120 mg / aq. NaOH / 3.5 h 8: 92 percent / pyridine / 2 h 9: 150 mg / CuCO3*Cu(OH)2 / quinoline / 2 h / 200 °C View Scheme

gardenoside (24512-62-7) → C16H20(2)H2O9

Conditions	Yield
Multi-step reaction with 6 steps 1: 73 percent / NaIO4 / aq. phosphate buffer / 0.25 h / 20 °C / pH 6.0 2: 88 percent / pyridine / 0.25 h 3: NaBD4 / methanol 4: 47 percent / aq. NaOH; (n-Bu)4NHSO4 / toluene / 3 h / 20 °C 5: quinoline / 1.5 h / 200 °C 6: AcOH / methanol View Scheme

gardenoside (24512-62-7) → C15H18(2)H2O9

Conditions	Yield
Multi-step reaction with 7 steps 1: 73 percent / NaIO4 / aq. phosphate buffer / 0.25 h / 20 °C / pH 6.0 2: 88 percent / pyridine / 0.25 h 3: NaBD4 / methanol 4: 47 percent / aq. NaOH; (n-Bu)4NHSO4 / toluene / 3 h / 20 °C 5: quinoline / 1.5 h / 200 °C 6: AcOH / methanol 7: 160 mg / aq. NaOH View Scheme

gardenoside (24512-62-7) → C22H26(2)H2O11

Conditions	Yield
Multi-step reaction with 9 steps 1: 73 percent / NaIO4 / aq. phosphate buffer / 0.25 h / 20 °C / pH 6.0 2: 88 percent / pyridine / 0.25 h 3: NaBD4 / methanol 4: 47 percent / aq. NaOH; (n-Bu)4NHSO4 / toluene / 3 h / 20 °C 5: quinoline / 1.5 h / 200 °C 6: AcOH / methanol 7: 160 mg / aq. NaOH 8: 92 percent / pyridine / 2 h 9: 163 mg / CuCO3*Cu(OH)2 / quinoline / 2 h / 200 °C View Scheme

gardenoside (24512-62-7) → 10-nor-geniposidic acid tetra-acetate

Conditions	Yield
Multi-step reaction with 8 steps 1: 73 percent / NaIO4 / aq. phosphate buffer / 0.25 h / 20 °C / pH 6.0 2: 88 percent / pyridine / 0.25 h 3: 94 percent / NaBH4 / methanol / 0.08 h 4: 57 percent / aq. NaOH; (n-Bu)4NHSO4 / toluene / 3 h / 20 °C 5: quinoline / 1.5 h / 200 °C 6: AcOH / methanol / 17 h 7: 120 mg / aq. NaOH / 3.5 h 8: 92 percent / pyridine / 2 h View Scheme

gardenoside (24512-62-7) → (1S,4aS,7aR)-1-((2S,3R,4S,5R,6R)-6-Hydroxymethyl-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions	Yield
Multi-step reaction with 5 steps 1: 73 percent / NaIO4 / aq. phosphate buffer / 0.25 h / 20 °C / pH 6.0 2: 88 percent / pyridine / 0.25 h 3: 94 percent / NaBH4 / methanol / 0.08 h 4: 57 percent / aq. NaOH; (n-Bu)4NHSO4 / toluene / 3 h / 20 °C 5: quinoline / 1.5 h / 200 °C View Scheme

gardenoside (24512-62-7) → [6β,8-2H2]-10-nor-geniposidic acid tetraacetate

Conditions	Yield
Multi-step reaction with 8 steps 1: 73 percent / NaIO4 / aq. phosphate buffer / 0.25 h / 20 °C / pH 6.0 2: 88 percent / pyridine / 0.25 h 3: NaBD4 / methanol 4: 47 percent / aq. NaOH; (n-Bu)4NHSO4 / toluene / 3 h / 20 °C 5: quinoline / 1.5 h / 200 °C 6: AcOH / methanol 7: 160 mg / aq. NaOH 8: 92 percent / pyridine / 2 h View Scheme

gardenoside (24512-62-7) → C25H44(2)H2O9Si3

Conditions	Yield
Multi-step reaction with 5 steps 1: 73 percent / NaIO4 / aq. phosphate buffer / 0.25 h / 20 °C / pH 6.0 2: 88 percent / pyridine / 0.25 h 3: NaBD4 / methanol 4: 47 percent / aq. NaOH; (n-Bu)4NHSO4 / toluene / 3 h / 20 °C 5: quinoline / 1.5 h / 200 °C View Scheme

gardenoside (24512-62-7) → randioside tetra-O-trimethylsilylether

Conditions	Yield
Multi-step reaction with 2 steps 1: 73 percent / NaIO4 / aq. phosphate buffer / 0.25 h / 20 °C / pH 6.0 2: 88 percent / pyridine / 0.25 h View Scheme

gardenoside (24512-62-7) → tetrahydrorandioside tetra-O-trimethylsilylether

Conditions	Yield
Multi-step reaction with 3 steps 1: 73 percent / NaIO4 / aq. phosphate buffer / 0.25 h / 20 °C / pH 6.0 2: 88 percent / pyridine / 0.25 h 3: 94 percent / NaBH4 / methanol / 0.08 h View Scheme

gardenoside (24512-62-7) → [6β,3β-2H2]-tetrahydrorandioside tetra-O-trimethylsilylether

Conditions	Yield
Multi-step reaction with 3 steps 1: 73 percent / NaIO4 / aq. phosphate buffer / 0.25 h / 20 °C / pH 6.0 2: 88 percent / pyridine / 0.25 h 3: NaBD4 / methanol View Scheme

gardenoside (24512-62-7) → (1S,4aS,7aS)-7-Methylsulfanylthiocarboxyoxy-1-((2S,3R,4S,5R,6R)-6-methylsulfanylthiocarboxyoxymethyl-3,4,5-tris-trimethylsilanyloxy-tetrahydro-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Conditions	Yield
Multi-step reaction with 4 steps 1: 73 percent / NaIO4 / aq. phosphate buffer / 0.25 h / 20 °C / pH 6.0 2: 88 percent / pyridine / 0.25 h 3: 94 percent / NaBH4 / methanol / 0.08 h 4: 57 percent / aq. NaOH; (n-Bu)4NHSO4 / toluene / 3 h / 20 °C View Scheme

gardenoside (24512-62-7) → C29H50(2)H2O10S4Si3

Conditions	Yield
Multi-step reaction with 4 steps 1: 73 percent / NaIO4 / aq. phosphate buffer / 0.25 h / 20 °C / pH 6.0 2: 88 percent / pyridine / 0.25 h 3: NaBD4 / methanol 4: 47 percent / aq. NaOH; (n-Bu)4NHSO4 / toluene / 3 h / 20 °C View Scheme

Upstream product

• 82426-17-3 <4-¹³C>-10-hydroxygeraniol 
• 69252-86-4 <10-(3)H>-10-hydroxygeraniol 
• 26488-97-1 8-hydroxygeraniol 
• 82426-06-0 <2-¹³C>-9,10-dihydroxygeraniol 
• 82426-23-1 <4-(13)C>-10-hydroxygeraniol 
• 82426-15-1 (R)-(+)-<9-¹³C>-10-hydroxycitronellol 
• 82426-16-2 (S)-(-)-<9-¹³C>-10-hydroxycitronellol 
• 82426-07-1 9,10-dihydroxygeraniol 
• 82345-51-5 10-dehydrogardenoside 

Downstream Products

• 82345-53-7 randioside 

Relevant articles and documents

Studies on Monoterpene Glucosides and Related Natural Products. LV. Iridane Skeleton Formation from Acyclic Monoterpenes in the Biosynthesis of Iridoid Glucosides in Gardenia jasminoides f. grandiflora Cell Suspension Cultures

Administration of (3)H- or (13)C-labeled acyclic monoterpenes to Gardenia jasminoides f. grandiflora cell suspension cultures showed that tarennoside (20) and gardenoside (21) were biosynthesized in the cell cultures via the cyclization of 10-oxogeranial (5a)/10-oxoneral (5b) to iridodial cation (14), followed by extensive randomization of the carbon atoms 3 and 11.Furthermore, the intermediacy of (R)-(+)- and (S)-(-)-10-hydroxycitronellol (24a, 24b) and (R)-(+)- and (S)-(-)-9,10-dihydroxycitronellol (28a, 28b) was disproved.Keywords - iridoid glucoside; biosynthesis; iridane skeleton formation; 10-oxocitral; iridodial cation; tarennoside; Gardenia jasminoides; cell culture