Product Name

  • Name

    GARDENOSIDE

  • EINECS
  • CAS No. 24512-62-7
  • Article Data2
  • CAS DataBase
  • Density 1.61 g/cm3
  • Solubility
  • Melting Point 118-120ºC
  • Formula C17H24 O11
  • Boiling Point 672.8 °C at 760 mmHg
  • Molecular Weight 404.371
  • Flash Point 242.1 °C
  • Transport Information
  • Appearance Powder.
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 24512-62-7 (GARDENOSIDE)
  • Hazard Symbols
  • Synonyms Cyclopenta[c]pyran-4-carboxylicacid, 1-(b-D-glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)-,methyl ester, [1S-(1a,4aa,7a,7aa)]-; Gardenoside (8CI); NSC 325664
  • PSA 175.37000
  • LogP -3.25830

Synthetic route

10-dehydrogardenoside
82345-51-5

10-dehydrogardenoside

gardenoside
24512-62-7

gardenoside

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol for 1h; Ambient temperature;
gardenoside
24512-62-7

gardenoside

randioside

randioside

Conditions
ConditionsYield
With sodium periodate In phosphate buffer at 20℃; for 0.25h; pH=6.0; Oxidation;73%
gardenoside
24512-62-7

gardenoside

A

D-Glucose
2280-44-6

D-Glucose

B

(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

(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

Conditions
ConditionsYield
With β-glucosidase In water at 37℃; for 2h;
gardenoside
24512-62-7

gardenoside

6-deoxyretzioside

6-deoxyretzioside

Conditions
ConditionsYield
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

gardenoside

[6β,8-2H2]-6-deoxyretzioside

[6β,8-2H2]-6-deoxyretzioside

Conditions
ConditionsYield
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

gardenoside

(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

(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
ConditionsYield
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

gardenoside

10-nor-geniposidic acid

10-nor-geniposidic acid

Conditions
ConditionsYield
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

gardenoside

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

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
ConditionsYield
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

gardenoside

C16H20(2)H2O9

C16H20(2)H2O9

Conditions
ConditionsYield
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

gardenoside

C15H18(2)H2O9

C15H18(2)H2O9

Conditions
ConditionsYield
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

gardenoside

C22H26(2)H2O11

C22H26(2)H2O11

Conditions
ConditionsYield
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

gardenoside

10-nor-geniposidic acid tetra-acetate

10-nor-geniposidic acid tetra-acetate

Conditions
ConditionsYield
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

gardenoside

(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

(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
ConditionsYield
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

gardenoside

[6β,8-2H2]-10-nor-geniposidic acid tetraacetate

[6β,8-2H2]-10-nor-geniposidic acid tetraacetate

Conditions
ConditionsYield
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

gardenoside

C25H44(2)H2O9Si3

C25H44(2)H2O9Si3

Conditions
ConditionsYield
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

gardenoside

randioside tetra-O-trimethylsilylether

randioside tetra-O-trimethylsilylether

Conditions
ConditionsYield
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

gardenoside

tetrahydrorandioside tetra-O-trimethylsilylether

tetrahydrorandioside tetra-O-trimethylsilylether

Conditions
ConditionsYield
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

gardenoside

[6β,3β-2H2]-tetrahydrorandioside tetra-O-trimethylsilylether

[6β,3β-2H2]-tetrahydrorandioside tetra-O-trimethylsilylether

Conditions
ConditionsYield
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

gardenoside

(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

(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
ConditionsYield
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

gardenoside

C29H50(2)H2O10S4Si3

C29H50(2)H2O10S4Si3

Conditions
ConditionsYield
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

Gardenoside Chemical Properties

Molecular Structure of Gardenoside (CAS NO.4165-96-2):

Molecular Formula: C17H24O11
Molecular Weight: 404.3659
IUPAC Name: methyl (1S,4aS,7S,7aS)-7-Hydroxy-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,7a-dihydro-1H-cyclopenta[c]pyran-4-carboxylate
Synonyms of Gardenoside (CAS NO.4165-96-2): 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 
CAS NO: 4165-96-2
Classification Code: Iridoids 
Index of Refraction: 1.643
Molar Refractivity: 90.35 cm3
Molar Volume: 249.6 cm3
Surface Tension: 87 dyne/cm
Density: 1.61 g/cm3
Flash Point: 242.1 °C
Enthalpy of Vaporization: 113.08 kJ/mol
Boiling Point: 672.8 °C at 760 mmHg
Vapour Pressure of Gardenoside (CAS NO.4165-96-2): 5.53E-21 mmHg at 25°C 

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