14216-03-6

Basic information

• Product Name: Hederacoside C
• Synonyms: HEDERACOSIDE C;Olean-12-en-28-oic acid, 3-[[2-O-(6-deoxy-alpha-l-mannopyranosyl)-alpha-l-arabinopyranosyl]oxy]-23-hydroxy-, O-6-deoxy-alpha-l-mannopyranosyl-(1->4)-O-beta-d-glucopyranosyl-(1->6)-beta-d-glucopyranosyl ester, (3beta,4alpha)-;kalopanax saponin B;(3beta,4alpha)-3-[[2-O-(6-Deoxy-alpha-l-mannopyranosyl)-alpha-l-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-28-oic acid O-6-deoxy-alpha-l-mannopyranosyl-(1->4)-O-beta-d-glucopyranosyl-(1->6)-beta-d-glucopyranosyl ester;KIZUTA SAPONIN K(12;HEDERACOSIDE C WITH HPLC;3-[[2-O-(α-L-Rhamnopyranosyl)-α-L-arabinopyranosyl]oxy]-23-hydroxyolean-12-en-28-oic acid 6-O-[4-O-(α-L-rhamnopyranosyl)-β-D-glucopyranosyl]-β-D-glucopyranosyl ester;3-O-α-L-Rhamnopyranosyl(1→2)-α-L-arabinopyranosylhederagenin 28-O-α-L-rhamnopyranosyl(1→4)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl
• CAS NO: 14216-03-6
• Molecular Formula: C₅₉H₉₆O₂₆
• Molecular Weight: 1221.38
• EINECS: 238-072-2
• Product Categories: AliphaticAnalytical Standards;Herbal DrugsChromatography;Alcohols;Chemical Class;EstersAlphabetic;H;HA -HTChemical Class;Heterocyclics;Life Sciences Standards;Natural Compounds;Natural CompoundsChemical Class;Natural Terpene StandardsChemical Class;Oxygen containingChemical Class;Polyhydroxy compoundsMore...Close...;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 14216-03-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 222 °C (dec.)(lit.)
• Appearance: /
• Density: 1.48 g/cm³
• Refractive Index: 1.637
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated), Pyridine (Sparingly)
• PKA: 12.50±0.70(Predicted)
• Stability: Hygroscopic
• BRN: 4229541
• CAS DataBase Reference: Hederacoside C(CAS DataBase Reference)
• NIST Chemistry Reference: Hederacoside C(14216-03-6)
• EPA Substance Registry System: Hederacoside C(14216-03-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 14216-03-6(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 14216-03-6 differently. You can refer to the following data:
1. solubilizer, bio-availability enhancer in oral suspensions, capsules
2. Hederacoside C is a Hedera helix leaf which has been used in botanical drug formulations to treat acute respiratory infection and bronchitis. Anti-myocardial.

InChI:InChI=1/C59H96O26/c1-24-34(63)38(67)42(71)49(78-24)83-46-29(20-60)80-48(45(74)41(46)70)77-22-30-37(66)40(69)44(73)51(81-30)85-53(75)59-17-15-54(3,4)19-27(59)26-9-10-32-55(5)13-12-33(56(6,23-61)31(55)11-14-58(32,8)57(26,7)16-18-59)82-52-47(36(65)28(62)21-76-52)84-50-43(72)39(68)35(64)25(2)79-50/h9,24-25,27-52,60-74H,10-23H2,1-8H3/t24-,25-,27?,28-,29+,30+,31?,32+,33-,34-,35-,36-,37+,38+,39+,40-,41+,42+,43+,44+,45+,46+,47+,48+,49-,50-,51-,52-,55-,56-,57+,58+,59-/m0/s1

Synthetic route

hederagenin-3-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1->4)-O-6-O-acetyl-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester (97240-03-4) → HN-saponin P (14216-03-6)

Conditions	Yield
With potassium hydroxide for 20h; Ambient temperature;	12 mg
With potassium hydroxide for 20h; Ambient temperature;	14 mg
With ammonia In ethanol; water at 20℃;

3-O-β-D-glucopyranosyl (1-4)-β-D-xylopyranosyl (1-3)-α-L-rhamnopyranosyl (1-2)-α-L-arabinopyranosyl-23-hydroxyolean-12-en-28-O-α-L-rhamnopyranosyl (1-4)-β-D-glucopyranosyl (1-6)-β-D-glucopyranosyl ester → HN-saponin P (14216-03-6) + hederagenin-3-O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester (119742-55-1) + alpha-Hederin (27013-91-8) + hederagenin 3-O-β-D-glucopyranosyl-(1->4)-O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranoside (904684-90-8)

Conditions	Yield
With Eubacterium A44; general anaerobic medium at 37℃; for 20h; Product distribution; Further Variations:; Reagents;	A 0.00415 mmol B 0.00279 mmol C 0.00099 mmol D 0.00428 mmol

HN-saponin P (14216-03-6) → dipsacoside B (33289-85-9) + prosapogenin (17184-21-3) + hederagenin 28-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester (99624-66-5) + alpha-Hederin (27013-91-8)

Conditions	Yield
With sulfuric acid In ethanol for 2h; Heating; Further byproducts given;	A 270 mg B n/a C 135 mg D n/a

HN-saponin P (14216-03-6) → prosapogenin (17184-21-3) + 3-O-<α-L-arabinopyranosyl>hederagenin 28-O-<β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside> (39524-08-8) + hederagenin 28-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester (99624-66-5) + alpha-Hederin (27013-91-8)

Conditions	Yield
With sulfuric acid In ethanol for 2h; Heating; Further byproducts given;	A n/a B 180 mg C 135 mg D n/a

HN-saponin P (14216-03-6) → prosapogenin (17184-21-3) + hederagenin 28-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester (99624-66-5) + 3β,23-dihydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl ester (57539-70-5) + alpha-Hederin (27013-91-8)

Conditions	Yield
With sulfuric acid In ethanol for 2h; Heating; Further byproducts given;	A n/a B 135 mg C 155 mg D n/a

HN-saponin P (14216-03-6) → prosapogenin (17184-21-3) + hederagenin 28-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester (99624-66-5) + cauloside D (12672-45-6) + alpha-Hederin (27013-91-8)

Conditions	Yield
With sulfuric acid In ethanol for 2h; Heating; Further byproducts given;	A n/a B 135 mg C n/a D n/a

HN-saponin P (14216-03-6) → hedaragenin (465-99-6) + prosapogenin (17184-21-3)

Conditions	Yield
With Bacteroides JY-6; Bifidobacterium K-111 In various solvent(s) at 37℃; for 36h;	A 24 mg B 8 mg

HN-saponin P (14216-03-6) → alpha-Hederin (27013-91-8)

Conditions	Yield
With potassium hydroxide; water for 1h; Heating;	40 mg
With potassium hydroxide In methanol; water at 100℃; for 2h;
With ammonium hydroxide In ethanol for 15h; Reflux;

HN-saponin P (14216-03-6) → prosapogenin (17184-21-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 180 mg / 0.05 N H2SO4 / ethanol / 2 h / Heating 2: 35 mg / cellulase / acetic acid; H2O / 15 h / 37 °C View Scheme

HN-saponin P (14216-03-6) → 3β-[(α-L-arabinopyranosyl)oxy]-23-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranosyl ester (39524-13-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 180 mg / 0.05 N H2SO4 / ethanol / 2 h / Heating 2: 15 mg / cellulase / acetic acid; H2O / 15 h / 37 °C View Scheme

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione (58-08-2) + HN-saponin P (14216-03-6) → C8H10N4O2*2C59H96O26

Conditions	Yield
In water at 20 - 22℃; for 0.666667h;

2-amino-1,9-dihydro-6H-purin-6-one (73-40-5) + HN-saponin P (14216-03-6) → C5H5N5O*C59H96O26

Conditions	Yield
In ethanol; chloroform; water at 40℃; for 1.5h;

HN-saponin P (14216-03-6) + adenine (66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9) → C5H5N5*C59H96O26

Conditions	Yield
In ethanol; chloroform; water at 40℃; for 1.5h;

HN-saponin P (14216-03-6) + β-glycyrrhizic acid monoammonium salt → C59H96O26*C42H62O16*H3N

Conditions	Yield
In water at 22℃; pH=7.2; Thermodynamic data;

cholesterol (57-88-5) + HN-saponin P (14216-03-6) → C59H96O26*C27H46O

Conditions	Yield
In ethanol; chloroform; water at 40℃; for 1.5h;

Upstream product

• 97240-03-4 hederagenin-3-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1->4)-O-6-O-acetyl-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester 

Downstream Products

• 17184-21-3 prosapogenin 
• 27013-91-8 alpha-Hederin 
• 465-99-6 hedaragenin 
• 99624-66-5 hederagenin 28-O-β-D-glucopyranosyl-(1->6)-O-β-D-glucopyranosyl ester 
• 12672-45-6 cauloside D 
• 57539-70-5 3β,23-dihydroxyolean-12-en-28-oic acid O-α-L-rhamnopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl ester 
• 39524-08-8 3-O-<α-L-arabinopyranosyl>hederagenin 28-O-<β-D-glucopyranosyl-(1-6)-β-D-glucopyranoside> 
• 33289-85-9 dipsacoside B 

Relevant articles and documents

Triterpene glycosides from Kalopanax septemlobum. 1. Glycosides A, B, C, F, G1, G2, I2, H, and J from leaves of Kalopanax septemlobum var. maximowichii introduced to Crimea

Eight known glycosides of hederagenin and the new triterpene glycoside 3-O-β-D-xylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2) -O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4) -O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin were isolated by chromatographic methods from leaves of Kalopanax septemlobum var. maximowichii introduced to Crimea. The known 3-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4) -O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin was observed for the first time in Kalopanax septemlobum. 2005 Springer Science + Business Media, Inc.

Studies on nepalese crude drugs. III. On the saponins of Hedera nepalensis K. KOCH.

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