CAS No.24512-62-7,GARDENOSIDE Suppliers

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Basic Information

Molecular Structure:
CAS No.:	24512-62-7
Name:	GARDENOSIDE
Article Data:	2

Formula:	C17H24 O11
Molecular Weight:	404.371
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
Density:	1.61 g/cm³
Melting Point:	118-120ºC
Boiling Point:	672.8 °C at 760 mmHg
Flash Point:	242.1 °C
Appearance:	Powder.
PSA:	175.37000
LogP:	-3.25830

Synthetic route

: 82345-51-5
10-dehydrogardenoside

: 24512-62-7
gardenoside

Conditions

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

: 24512-62-7
gardenoside

: randioside

Conditions

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

: 24512-62-7
gardenoside

A: 2280-44-6
D-Glucose

B: 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

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

: 24512-62-7
gardenoside

: 6-deoxyretzioside

Conditions

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

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

: 24512-62-7
gardenoside

: [6β,8-2H2]-6-deoxyretzioside

Conditions

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

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

: 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

Conditions

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

: 24512-62-7
gardenoside

: 10-nor-geniposidic acid

Conditions

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

: 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

Conditions

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

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

: 24512-62-7
gardenoside

: C16H20(2)H2O9

Conditions

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

: 24512-62-7
gardenoside

: C15H18(2)H2O9

Conditions

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

Raw Materials

82426-07-1

26488-97-1

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Chemistry

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