Rebaudioside A - analytical standard, ≥97% , CAS No.58543-16-1

CAS: 58543-16-1 Cat. No.: R107557 Formula: C₄₄H₇₀O₂₃ Peso molecolare: 967.01 Beilstein Registry Number: 6470556 Numero EC: 611-696-6 PubChem CID: 6918840

GRADE & PURITY Analytical standard, ≥97%

Synonyms

DTXSID8047898 | B3FUD0528F | 1-O-(13alpha-{[beta-D-glucopyranosyl-(1->2)-[beta-D-glucopyranosyl-(1->3)]-beta-D-glucopyranosyl]oxy}-18-oxo-5beta,8alpha,9beta,10alpha-kaur-16-en-18-yl)-beta-D-glucopyranose | Chrysanta AR-P | DTXCID50819922 | CBDivE_001904 |

Storage

Room temperature

Shipped In

Normal

Specifications

Sinonimi

DTXSID8047898 | B3FUD0528F | 1-O-(13alpha-{[beta-D-glucopyranosyl-(1->2)-[beta-D-glucopyranosyl-(1->3)]-beta-D-glucopyranosyl]oxy}-18-oxo-5beta,8alpha,9beta,10alpha-kaur-16-en-18-yl)-beta-D-glucopyranose | Chrysanta AR-P | DTXCID50819922 | CBDivE_001904 |

Specifiche e purezza

analytical standard, ≥97%

Condizioni di conservazione di stoccaggio

Room temperature

Spedito in

Normal

Grado

Standard analitico

Purezza

≥97%

Nomi e identificatori

• Pubchem Sid: 508810321
• Sorrisi canonici: CC12CCCC(C1CCC34C2CCC(C3)(C(=C)C4)OC5C(C(C(C(O5)CO)O)OC6C(C(C(C(O6)CO)O)O)O)OC7C(C(C(C(O7)CO)O)O)O)(C)C(=O)OC8C(C(C(C(O8)CO)O)O)O
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-3,4-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• InChIKey: HELXLJCILKEWJH-NCGAPWICSA-N
• INCHI: 1S/C44H70O23/c1-17-11-43-9-5-22-41(2,7-4-8-42(22,3)40(59)66-38-33(58)30(55)26(51)20(14-47)62-38)23(43)6-10-44(17,16-43)67-39-35(65-37-32(57)29(54)25(50)19(13-46)61-37)34(27(52)21(15-48)63-39)64-36-31(56)28(53)24(49)18(12-45)60-36/h18-39,45-58H,1,4-16H2,2-3H3/t18-,19-,20-,21-,22+,23+,24-,25-,26-,27-,28+,29+,30+,31-,32-,33-,34+,35-,36+,37+,38+,39+,41-,42-,43-,44+/m1/s1
• Isomeri SMILES: C[C@@]12CCC[C@@]([C@H]1CC[C@]34[C@H]2CC[C@](C3)(C(=C)C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)(C)C(=O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O
• WGK Germania: 3
• RTECS: NZ8174800
• PubChem CID: 6918840
• Peso molecolare: 967.01
• Beilstein: 6470556
• Reaxy-Rn: 6470556

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Prenol lipids
      • Subclass Terpene glycosides
        • Level5 Diterpene glycosides
          • Level6 Steviol glycosides

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Prenol lipids
• Subclass: Terpene glycosides
• Intermediate Tree Nodes: Diterpene glycosides
• Direct Parent: Steviol glycosides
• Alternative Parents: Oligosaccharides Kaurane diterpenoids Fatty acyl glycosides O-glycosyl compounds Oxanes Secondary alcohols Carboxylic acid esters Polyols Oxacyclic compounds Monocarboxylic acids and derivatives Acetals Primary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Steviol glycoside - Oligosaccharide - Diterpenoid - Kaurane diterpenoid - Fatty acyl glycoside - Glycosyl compound - O-glycosyl compound - Fatty acyl - Oxane - Carboxylic acid ester - Secondary alcohol - Oxacycle - Monocarboxylic acid or derivatives - Organoheterocyclic compound - Acetal - Carboxylic acid derivative - Polyol - Organooxygen compound - Organic oxygen compound - Organic oxide - Alcohol - Hydrocarbon derivative - Carbonyl group - Primary alcohol - Aliphatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as steviol glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically linked to a steviol (a diterpenoid based on a 13-Hydroxykaur-16-en-18-oic acid) moiety.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Rotazione specifica [α]: -33° (C=1,H2O)
• Punto di fusione (°C): 235°C(lit.)
• Peso molecolare: 967.000 g/mol
• XLogP3: -2.800
• Hydrogen Bond Donor Count: 14
• Hydrogen Bond Acceptor Count: 23
• Rotatable Bond Count: 13
• Exact Mass: 966.431 Da
• Monoisotopic Mass: 966.431 Da
• Topological Polar Surface Area: 374.000 Ų
• Heavy Atom Count: 67
• Formal Charge: 0
• Complexity: 1760.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 26
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Riferimenti

1. Hongmei Zhang, Shixin Sun, Yanqing Wang, Zhenghao Fei, Jian Cao.  (2018)  Binding mechanism of five typical sweeteners with bovine serum albumin.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:30015031] [10.1016/j.saa.2018.07.013]

2. Yuxin Wang, Linyao Li, Yawen Wang, Xiaokang Zhu, Mingdong Jiang, Erqun Song, Yang Song.  (2018)  New application of the commercial sweetener rebaudioside a as a hepatoprotective candidate: Induction of the Nrf2 signaling pathway.  EUROPEAN JOURNAL OF PHARMACOLOGY,      [PMID:29355553] [10.1016/j.ejphar.2018.01.020]

3. Jingle Jiang, Lina Qi, Quanwei Wei, Fangxiong Shi.  (2017)  Effects of daily exposure to saccharin sodium and rebaudioside A on the ovarian cycle and steroidogenesis in rats.  REPRODUCTIVE TOXICOLOGY,      [PMID:29262312] [10.1016/j.reprotox.2017.12.006]

4. Chengzhi Liu, Mengchu Niu, Yibing Wang, Lingyi Ren, Yueyue Li, Nan Jiang, Chunxuan Wu, Niu Liu, Yanwen Zhang, Jiakang He.  (2025)  Self-Assembled Rebaudioside A Nanomicelles: A Novel Delivery System for Mangiferin to Increase Oral Bioavailability.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:40608013] [10.1021/acs.jafc.5c05528]