(1R,5R,9S,13S)-13-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid

Base Information

• Chemical Name: (1R,5R,9S,13S)-13-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid
• CAS No.: 41093-60-1
• Molecular Formula: C32H50O13
• Molecular Weight: 642.741
• Hs Code.: 29389090
• European Community (EC) Number: 817-155-2
• Mol file: 41093-60-1.mol

Synonyms:C32H50O13;41093-60-1

Chemical Property of (1R,5R,9S,13S)-13-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid

Chemical Property:

• Vapor Pressure: 2.19E-33mmHg at 25°C
• Melting Point: 190oC (methanol )
• Boiling Point: 847.3°Cat760mmHg
• PKA: 4.63±0.60(Predicted)
• Flash Point: 267.6°C
• PSA: 215.83000
• Density: 1.45g/cm³
• LogP: -0.19660
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 7
• Exact Mass: 642.32514165
• Heavy Atom Count: 45
• Complexity: 1150

Purity/Quality:

≥98% ^*data from raw suppliers

Steviolbioside ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC(C1CCC34C2CCC(C3)(C(=C)C4)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)(C)C(=O)O
• Isomeric SMILES: C[C@@]12CCC[C@@](C1CC[C@]34C2CC[C@](C3)(C(=C)C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)(C)C(=O)O
• Uses: Steviolbioside is a terpenoid compound which is converted into antituberculotic and antibacterial agents. In addition it is used as a natural sweetener.

Technology Process of (1R,5R,9S,13S)-13-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylic acid

There total 13 articles about (1R,5R,9S,13S)-13-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-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: 95.0%

stevioside (57817-89-7,66537-21-1,71030-71-2,92216-43-8,92216-44-9,142481-99-0) → 13-O-β-sophorosyl-steviol (41093-60-1)

Guidance literature:

With potassium hydroxide; at 100 ℃; for 1h;

Reference yield: 87.5%

stevioside (57817-89-7) → steviolbioside (41093-60-1)

Guidance literature:

With sodium hydroxide; In methanol; at 60 ℃; for 7h;

DOI:10.1016/j.foodchem.2014.10.093

Reference yield: 45.0%

13-O-<2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl>-steviol methyl ester (77614-27-8) → steviolbioside (41093-60-1)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; at -30 ℃; for 3h;

DOI:10.1016/0040-4020(80)80136-0

upstream raw materials:

13-O-<2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-β-D-glucopyranosyl>-steviol methyl ester

13-O-β-sophorosyl-19-O-β-isomaltosyl-steviol

3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose

methyl (4R,4aS,6aR,9S,11aR,11bS)-9-hydroxy-4,11b-dimethyl-8-methylenetetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylate

Downstream raw materials:

19-O-<3-<(benzyloxycarbonyl)amino>-3-carbomethoxypropyl>steviolbioside

catecholyl 19-O-(3-sulfo-3-kaliosulfopropyl)steviolbioside

13-O-[β-D-soforosyl]-benzyl-ent-kauren-19-oate

D-glucose

Refernces

• 1、 Well, Caroline,Frank, Oliver,Hofmann, Thomas. "Quantitation of sweet steviol glycosides by means of a HILIC-MS/MS-SIDA approach". . p. 11312 - 11320. Retrieved 2013.
• 2、 Kataev,Strobykina,Andreeva,Garifullin,Sharipova,Mironov,Chestnova. "Synthesis and antituberculosis activity of derivatives of Stevia rebaudiana glycoside steviolbioside and diterpenoid isosteviol containing hydrazone, hydrazide, and pyridinoyl moieties". . p. 483 - 491. Retrieved 2011.
• 3、 Lobov,Kasai,Ohtani,Tanaka,Yamasaki. "Enzymic production of sweet stevioside derivatives: transglucosylation by glucosidases.". . p. 2959 - 2965. Retrieved 1991.
• 4、 Sharipova,Garifullin,Andreeva,Strobykina, I. Yu.,Kataev. "Synthesis of thiazolylhydrazones of the Stevia rebaudiana glycoside steviolbioside". . . Retrieved 2016.
• 5、 -. "INHIBITORS OF ANTIBIOTIC RESISTANCE MEDIATED BY ARN T". Page/Page column 27-28. . Retrieved 2021/01/29.
• 6、 Sharipova,Andreeva,Strobykina, I. Yu.,Voloshina,Strobykina,Kataev. "Synthesis and Antimicrobial Activity of Glucuronosyl Derivatives of Steviolbioside from Stevia rebaudiana". . p. 1107 - 1111. Retrieved 2017/11/27.