27013-91-8

Basic information

• Product Name: ALPHA-HEDERIN
• Synonyms: ALPHA-HEDERIN;HELIXIN;HEDERIN, ALPHA-;(3-beta,4-alpha)-nopyranosyl)oxy)-23-hydroxy;akebiasaponinpd;akebosidestc;alpha-hederine;glycosidel-e1
• CAS NO: 27013-91-8
• Molecular Formula: C₄₁H₆₆O₁₂
• Molecular Weight: 764.98
• EINECS: 248-166-5
• Product Categories: Tri-Terpenoids;Saponins;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 27013-91-8.mol
• Article Data: 17

Chemical Properties

• Melting Point: 215°C (dec.)
• Boiling Point: 849.6oC at 760 mmHg
• Flash Point: 250.7oC
• Appearance: /
• Density: 1.32
• Vapor Pressure: 1.4E-33mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: 2-8°C
• PKA: 4.63±0.70(Predicted)
• CAS DataBase Reference: ALPHA-HEDERIN(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-HEDERIN(27013-91-8)
• EPA Substance Registry System: ALPHA-HEDERIN(27013-91-8)

Safety Data

• Statements: 22
• Safety Statements: 22-45-24/25
• RIDADR: 1544
• WGK Germany: 3
• RTECS: RK0177800
• Hazardous Substances Data: 27013-91-8(Hazardous Substances Data)

Usage

Uses

α-Hederin is a saponin of dry extracts from the leaves of Hedera helix L.Inhibitor of β2-adrenergic receptor-GFP fusion proteins. Potential cause for asphyxiation.

Definition

ChEBI: A triterpenoid saponin that is hederagenin attached to a 2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl residue at position 3 via a glycosidic linkage. It has been isolated from the stem bark of Kalopanax pictus.

InChI:InChI=1/C41H66O12/c1-21-28(44)30(46)31(47)33(51-21)53-32-29(45)24(43)19-50-34(32)52-27-11-12-37(4)25(38(27,5)20-42)10-13-40(7)26(37)9-8-22-23-18-36(2,3)14-16-41(23,35(48)49)17-15-39(22,40)6/h8,21,23-34,42-47H,9-20H2,1-7H3,(H,48,49)/t21-,23?,24-,25?,26?,27-,28-,29-,30+,31+,32+,33?,34?,37-,38-,39+,40+,41-/m0/s1

Upstream product

• 76729-67-4 hederagenin 3-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranosyl-(1->4)-β-D-ribopyranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranoside 
• 60213-75-4 C₅₃H₇₈O₁₈ 
• 29781-27-9 C₅₂H₈₄O₂₁ 
• 33289-85-9 Dipsacosid B 
• 29321-28-6 hederogenin 3-O-β-D-xylopyranosyl-(1-3)-α-L-rhamnopyranosyl-(1-2)-α-L-arabinopyranoside 
• 76729-67-4 hederagenin 3-O-β-D-glucopyranosyl-(1-4)-β-D-glucopyranosyl-(1-4)-β-D-xylopyranosyl-(1-3)-α-L-rhamnopyranosyl-(1-2)-α-L-arabinopyranoside 
• 29781-27-9 hederagenin 3-O-β-D-glucopyranosyl-(1-4)-β-D-xylopyranosyl-(1-3)-α-L-rhamnopyranosyl-(1-2)-α-L-arabinopyranoside 
• 128717-92-0 3-O-α-L-rhamnopyranosyl(1->2)-α-L-arabinopyranosyl-hederagenin 28-O-β-D-xylopyranosyl(1->6)-β-D-glucopyranosyl ester 
• 942997-00-4 3-O-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranosyl hederagenin-28-O-β-D-galactopyranosyl-(1->6)-β-D-glucopyranosyl ester 
• 120481-41-6 3-O-<α-L-rhamnopyranosyl(1->2)-α-L-arabinopyranosyl>-28-O-<6-acetyl-β-D-glucopyranosyl(1->6)-β-D-glucopyranosyl>hederagenin 
• 87781-65-5 mukurozi-saponin Y₂ 
• 87733-79-7 hederagenin 3-O-(3,4-O-di-acetyl-α-L-arabinopyranoside)-(1->3)-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranoside 
• 904684-90-8 hederagenin 3-O-β-D-glucopyranosyl-(1->4)-O-β-D-xylopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->2)-O-α-L-arabinopyranoside 
• 14216-03-6 HN-saponin P 

Downstream Products

• 73-34-7 L-rhamnose 
• 87-72-9 L-(+)-arabinose 
• 465-99-6 hedaragenin 
• 465-99-6 3β,23-Dihydroxy-olean-12-en-28-oic acid 
• 17184-21-3 prosapogenin 
• 465-99-6 hederagenin 
• 128902-64-7 3-O-alpha-L-arabinopyranoside hederagenin 

Relevant articles and documents

Antifungal activity of modified hederagenin glycosides from the leaves of Kalopanax pictum var. chinense

Monodesmosides which were obtained from the partial degradation of hederagenin bisdesmosides exhibited significant antifungal effect against Microsporum canis, Coccidioides immitis, Trichophyton mentagrophytes, Cryptococcus neoformans, and Candida albican

Triterpene glycosides of Dipsacus azureus

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Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis

Investigation of the n-BuOH extract of the rhizomes of Anemone taipaiensis led to the isolation of five new oleanane-type triterpenoid saponins (1-5), together with seven known saponins (6-12). Their structures were determined by the extensive use of 1D and 2D NMR experiments along with ESIMS analyses and acid hydrolysis. The aglycone of 1, 2 and 4 was determined as siaresinolic acid, which was reported in this genus for the first time. The cytotoxicities of the saponins 1-12, prosapogenins 4a, 5a, 10a-12a and sapogenins siaresinolic acid (SA), oleanolic acid (OA), hederagenin (HE) were evaluated against five human cancer cell lines, including HepG2, HL-60, A549, HeLa and U87MG. The monodesmosidic saponins 6-8, 5a, 10a-12a and sapogenins SA, OA, HE exhibited cytotoxic activity toward all cancer cell lines, with IC 50 values ranging from 2.25 to 57.28 μM. Remarkably, the bisdesmosidic saponins 1-4 and 9 showed selective cytotoxicity against the U87MG cells.

Synthesis of α-hederin, δ-hederin, and related triterpenoid saponins

The synthesis of α-hederin (3-O-[α-L-rhamnopyranosyl-(1→2) -α-L-arabinopyranosyl]hederagenin, 1), δ-hederin (3-O-(α-L-arabinopyranosyl)hederagenin, 3), and three related triterpenoid saponins is described as part of a study of the structure-activity relationships between triterpenoid saponins and hemolytic activity. 4-Methoxybenzyl α-L-arabinopyranoside (11) was synthesized first and then used to prepare the different arabinose acceptors. Glycosylation between the acceptors and 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate (20) was performed in excellent yield to give the desired disaccharides. Coupling of the trichloroacetimidate derivatives of the disaccharides to allyl- or methyl-hederagenin gave the protected saponosides in high yields. The saponins and their corresponding methyl esters were then obtained in good to moderate yields after deprotection. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.