3,14-Dihydroxycard-20(22)-enolide

Base Information

• Chemical Name: 3,14-Dihydroxycard-20(22)-enolide
• CAS No.: 466-09-1
• Molecular Formula: C23H34 O4
• Molecular Weight: 374.521
• European Community (EC) Number: 207-373-0
• NSC Number: 119993,277290,224424
• DSSTox Substance ID: DTXSID60871617
• Wikidata: Q105345172
• Mol file: 466-09-1.mol

Synonyms:466-09-1;NSC277290;5alpha-Card-20(22)-enolide,14-dihydroxy-;5.alpha.-Card-20(22)-enolide,14-dihydroxy-;MLS002701726;3,14-Dihydroxycard-20(22)-enolide;Card-20(22)-enolide,14-dihydroxy-, (3.beta.,5.alpha.)-;NSC407806;NSC-119993;NSC-277290;ODORIGENINB;SCHEMBL1152954;DTXSID60871617;XZTUSOXSLKTKJQ-UHFFFAOYSA-N;NSC119993;NSC224424;UZARIGENIN B614014K070;AKOS032948827;NSC-224424;3-(3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl)-2H-furan-5-one;NCI60_002256;NCI60_003892;SMR001565322;B0005-190236;3-[(3S,5S,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one;4-(3,14-dihydroxy-10,13-dimethyl-hexadecahydrocyclopenta[a]phenanthren-17-yl)-5h-furan-2-one

Chemical Property of 3,14-Dihydroxycard-20(22)-enolide

Chemical Property:

• Melting Point: 240-256°
• Boiling Point: 549.3°Cat760mmHg
• PKA: 14.93±0.70(Predicted)
• Flash Point: 188.2°C
• PSA: 66.76000
• Density: 1.231g/cm³
• LogP: 3.60430
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 374.24570956
• Heavy Atom Count: 27
• Complexity: 686

Purity/Quality:

99%, ^*data from raw suppliers

Uzarigenin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2CCC4(C3(CCC4C5=CC(=O)OC5)O)C)O

Technology Process of 3,14-Dihydroxycard-20(22)-enolide

There total 32 articles about 3,14-Dihydroxycard-20(22)-enolide 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: 42.0%

odoroside K (9007-56-1,56783-03-0,88972-52-5,98775-41-8,128902-63-6,129830-68-8,129830-69-9,129893-56-7,143289-49-0) → uzarigenin 3-O-α-D-gentiodiginoside (9007-56-1,56783-03-0,88972-52-5,98775-41-8,128902-63-6,129830-68-8,129830-69-9,129893-56-7,143289-49-0) + 3β-hydroxy-5α-carda-14(15),20(22)-dienolide (3080-20-4) + uzarigenine (466-09-1)

Guidance literature:

at 290 ℃;

Reference yield: 35.0%

3β-O-(β-D-diginosyl)-14-hydroxy-5α,14β-card-20(22)-enolide (58407-69-5) → uzarigenine (466-09-1)

Guidance literature:

at 260 ℃;

Reference yield:

Uzarin (41628-29-9,58782-11-9) → D-Glucose (2280-44-6) + uzarigenine (466-09-1)

Guidance literature:

With extract of the sea snail Monodonta turbinata Born; In ethanol; xylene; at 40 ℃; for 24h; other reagent: aqueous extract of the sea snail Patella aspera Lamarck;

upstream raw materials:

3β-O-(β-D-diginosyl)-14-hydroxy-5α,14β-card-20(22)-enolide

3β-O-(β-D-digitalosyl)-14-hydroxy-5α,14β-card-20(22)-enolide

Uzarin

odoroside K

Downstream raw materials:

3-epidigitoxigenin

digitoxigenin myristate

digitoxigenin palmitate

digitoxigenin stearate

Refernces

• 1、 Kim, Youn Chul,Higuchi, Ryuichi,Komori, Tetsuya,Abe, Fumiko,Yamauchi, Tatsuo. "Degradation of Cardenolide Glycosides". . p. 943 - 947. Retrieved 2007/10/02.
• 2、 Petricic, J.,Kalogjera, Zdenka,Stanic, Gordana. "Conversion of glycosides to aglycones or shortened glycosides using a biocatalytically active extract from the sea snails Monodonta turbinata and Patella aspera". . p. 508. Retrieved 2007/10/02.