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

CAS: 58543-16-1 Cat. No.: R107559 Peso molecular: 967.01 Beilstein Registry Number: 6470556 Número EC: 611-696-6 PubChem CID: 6918840

GRADE & PURITY ≥97%

Synonyms

Reb A | Stevioside A3 | Glycoside A3

Storage

Room temperature

Shipped In

Normal

Specifications

Sinónimos

Reb A | Stevioside A3 | Glycoside A3

Especificaciones y pureza

≥97%

Mecanismos bioquímicos y fisiológicos

Rebaudioside A is a steviol glycoside and α-glucosidase inhibitor with an IC50 of 35.01 ug/mL.

Condiciones de almacenamiento de almacenamiento

Room temperature

Enviado en

Normal

Tipo de acción

INHIBITOR

Pureza

≥97%

Nombres e identificadores

• Pubchem Sid: 504764382
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504764382
• Sonrisas canónicas: 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
• Isómeros 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 Alemania: 3
• RTECS: NZ8174800
• PubChem CID: 6918840
• Peso molecular: 967.01
• Beilstein: 6470556
• Reaxy-Rn: 6470556

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: 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
• Descripción: 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

Propiedades químicas y físicas

• Solubilidad: Soluble in water
• Rotación específica [α]: -33° (C=1,H2O)
• Punto de fusión (°C): 235°C(lit.)
• Peso molecular: 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

Referencias

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]