10-[4,5-Dihydroxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Base Information

• Chemical Name: 10-[4,5-Dihydroxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS No.: 27013-91-8
• Molecular Formula: C41H66 O12
• Molecular Weight: 750.968
• Hs Code.: 29389090
• European Community (EC) Number: 248-166-5
• NSC Number: 106553
• DSSTox Substance ID: DTXSID20949785
• Wikipedia: %CE%91-Hederin
• Wikidata: Q105140097
• Metabolomics Workbench ID: 125952
• ChEMBL ID: CHEMBL1980760
• Mol file: 27013-91-8.mol

Synonyms:.alpha.-hederin;alpha-hederin;Pulsatilla saponin A;Rha-Ara-3beta-hederagenin

Chemical Property of 10-[4,5-Dihydroxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.4E-33mmHg at 25°C
• Melting Point: 215oC (dec.)
• Refractive Index: 1.601
• Boiling Point: 849.6oC at 760 mmHg
• PKA: 4.63±0.70(Predicted)
• Flash Point: 250.7oC
• PSA: 195.60000
• Density: 1.32g/cm3
• LogP: 3.52110
• Storage Temp.: 2-8°C
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 6
• Exact Mass: 750.45542754
• Heavy Atom Count: 53
• Complexity: 1440

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Alpha-Hederin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Low toxicity by ingestion.
• Hazard Codes: Low toxicity by ingestion.
• Statements: 22
• Safety Statements: 22-45-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)CO)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)O)C)C)C)O)O)O)O)O
• 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.

Technology Process of 10-[4,5-Dihydroxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

There total 36 articles about 10-[4,5-Dihydroxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

3-O-α-L-rhamnopyranosyl(1->2)-α-L-arabinopyranosyl-hederagenin 28-O-β-D-xylopyranosyl(1->6)-β-D-glucopyranosyl ester (128717-92-0) → kalopanaxsaponin A (27013-91-8,78174-42-2,83864-73-7) + methyl β-D-xylopyranosyl(1->6)-β-D-glucopyranoside (128779-40-8)

Guidance literature:

With 2,6-dimethylpyridine; lithium iodide; In methanol; for 16h; Heating;

DOI:10.1248/cpb.38.411

Reference yield:

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) → hedaragenin (465-99-6) + prosapogenin (17184-21-3) + sapindoside B (29321-28-6,72629-76-6,80666-65-5,30994-75-3) + alpha-Hederin (27013-91-8)

Guidance literature:

With Bacteroides JY-6; Bifidobacterium K-111; In various solvent(s); at 37 ℃; for 36h;

DOI:10.1248/bpb.21.360

Reference yield:

HN-saponin P (14216-03-6,27013-76-9) → dipsacoside B (33289-85-9,942997-00-4) + 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)

Guidance literature:

With sulfuric acid; In ethanol; for 2h; Further byproducts given; Heating;

DOI:10.1248/cpb.33.3473

upstream raw materials:

dipsacoside B

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

HN-saponin P

hederagenin 3-O-α-L-arabinofuranosyl-(1->3)-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranoside

Downstream raw materials:

L-rhamnose

L-(+)-arabinose

hedaragenin

3β,23-Dihydroxy-olean-12-en-28-oic acid

Refernces

• 1、 Akimaliev,Isaev,Abubakirov. "Structure of dipsacobioside". . p. 202 - 203. Retrieved 2002.
• 2、 Mukhamedziev et al.. "". . . Retrieved 1971.
• 3、 Sarkahya, Nazlboeke,Krmzguel, Sueheyla. "Antimicrobially active hederagenin glycosides from Cephalaria elmaliensis". . p. 828 - 833. Retrieved 2012.
• 4、 Grishkovets,Panov,Kachala,Shashkov. "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". . p. 194 - 199. Retrieved 2008/02/01.