Hederagenin

Base Information

• Chemical Name: Hederagenin
• CAS No.: 465-99-6
• Molecular Formula: C30H48O4
• Molecular Weight: 472.709
• Hs Code.: 29181990
• European Community (EC) Number: 207-369-9
• NSC Number: 24954
• UNII: RQF57J8212
• DSSTox Substance ID: DTXSID301029412
• Nikkaji Number: J1.536I
• Wikipedia: Hederagenin
• Wikidata: Q5697238
• Pharos Ligand ID: JF78HS6RFCJ4
• Metabolomics Workbench ID: 65202
• ChEMBL ID: CHEMBL486400
• Mol file: 465-99-6.mol

Synonyms:cyclocaric acid A;hederagenin

Chemical Property of Hederagenin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 332 - 334oC
• Refractive Index: 1.569
• Boiling Point: 589.4 °C at 760 mmHg
• PKA: 4.63±0.70(Predicted)
• Flash Point: 324.3 °C
• PSA: 77.76000
• Density: 1.14 g/cm³
• LogP: 6.20600
• Storage Temp.: 2-8°C
• Solubility.: methanol: soluble1mg/mL
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 472.35526001
• Heavy Atom Count: 34
• Complexity: 908

Purity/Quality:

5: 1, 10%, 2% C 1%, 5% C 3% ^*data from raw suppliers

Hederagenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 22
• Safety Statements: 22-45-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)O)C)C)C2C1)C)C(=O)O)C
• Isomeric SMILES: C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)C)(C)CO)O
• Description: Hederagenin is a triterpene saponin that has been found in P. eximia with diverse biological activities. It increases production of reactive oxygen species (ROS), reduces colony formation, and induces apoptosis in cisplatin-resistant head and neck carcinoma (HNC) cells. In vivo, hederagenin (50, 100, and 200 mg/kg) suppresses tumor growth in a cisplatin-resistant HNC mouse xenograft model. It reduces aortic atherosclerotic lesion area, serum cholesterol and LDL levels, and inducible nitric oxide synthase (iNOS) protein levels in a rat model of atherosclerosis. Hederagenin (50 mg/kg) reduces ethanol-induced production of TNF-α, IL-6, and COX-2, alcohol dehydrogenase 2 (ALDH2) mRNA expression, and liver damage in a rat model of alcohol-induced hepatotoxicity. It also induces autophagy and inhibits oligomerization of α-synuclein in a mouse model of Parkinson''s disease induced by MPTP.
• Uses: Triterpenoid which can inhibit the proliferation of leukemia HL-60 cells.

Technology Process of Hederagenin

There total 126 articles about Hederagenin 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: 14.0%

alpha-Hederin (27013-91-8) → hedaragenin (465-99-6) + prosapogenin (17184-21-3) + 3-O-alpha-L-arabinopyranoside hederagenin (128902-64-7)

Guidance literature:

at 280 ℃;

Reference yield:

HN-saponin P (14216-03-6,27013-76-9) → hedaragenin (465-99-6) + prosapogenin (17184-21-3)

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:

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

upstream raw materials:

gypsogenin

3β-(O⁵-β-D-glucopyranosyl-β-L-arabinofuranosyloxy)-23-hydroxy-olean-12-en-28-oic acid

diazomethane

prosapogenin

Downstream raw materials:

3,23-bis-benzoyloxy-olean-12-en-28-oic acid

7-chloro-[1]naphthol

2,7-dimethylnaphthalene

1,2,3,4-Tetramethylbenzene

Refernces

• 1、 Li, Wei,Ding, Yan,Sun, Ya Nan,Yan, Xi Tao,Yang, Seo Young,Choi, Chun Whan,Cha, Ji Yun,Lee, Young Mi,Kim, Young Ho. "Triterpenoid saponins of pulsatilla koreana root have inhibition effects of tumor necrosis factor-α secretion in lipopolysaccharide-induced RAW264.7 cells". . p. 471 - 476. Retrieved 2013.
• 2、 Kuang, Hai-Xue,Wang, Zhi-Bin,Wang, Qiu-Hong,Yang, Bing-You,Xiao, Hong-Bin,Okada, Yoshihito,Okuyama, Tohru. "Triterpene glucosides from the leaves of aralia elata and their cytotoxic activities". . p. 703 - 710. Retrieved 2013.
• 3、 Scheidegger,Cherbuliez. "-". . p. 547,554. Retrieved 1955.
• 4、 Watanabe, Kazuki,Mimaki, Yoshihiro,Sakuma, Chiseko,Sashida, Yutaka. "Eranthisaponins A and B, two new bisdesmosidic triterpene saponins from the tubers of Eranthis cilicica". . p. 879 - 882. Retrieved 2003.
• 5、 Annaev, Ch.,Isamukhamedova, M.,Abubakirov, N. K.. "TRITERPENE GLYCOSIDES OF Climacoptera transoxana. I.". . p. 190 - 194. Retrieved 1983.
• 6、 KHORANA,RAISINGHANI. "Studies of Luffa echinata. III. The oil and the saponin.". . p. 687 - 689. Retrieved 1961.
• 7、 Moffi Biang, Armand Emmanuel,Messi, Lin Marcellin,Le Doux Kamto, Eutrophe,Simo, Line Made,Lavedan, Pierre,Vedrenne, Marc,Mbing, Josephine Ngo,Pegnyemb, Dieudonné Emmanuel,Haddad, Mohamed,Noté, Olivier Placide. "Triterpenoid saponins and others glycosides from the stem barks of Pancovia turbinata Radlk". . . Retrieved 2021/07/19.
• 8、 Chulrik, Wanatsanan,Chunglok, Warangkana,Li, Jian-Xin,Suebsakwong, Parichat,Suksamrarn, Apichart,Yao, Zhu-Jun. "New triterpenoid saponin glycosides from the fruit fibers of: Trichosanthes cucumerina L.". . p. 10461 - 10470. Retrieved 2020/03/27.