D-Erythronolactone - ≥98%(GC) , CAS No.15667-21-7

CAS: 15667-21-7 Cat. No.: D130853 Molecular Weight: 118.09 Beilstein Registry Number: 81073

GRADE & PURITY ≥98%(GC)

Synonyms

3,4-Dihydroxyoxolan-2-onato(3-) | MFCD00077763 | s11960 | Sedotussin (TN) | Q27159785 | SCHEMBL818248 | Carbamazepine10,11-Epoxide | Rel-(3R,4R)-3,4-dihydroxydihydrofuran-2(3H)-one | Erythronic acid g-lactone | d-erythrono-1,4-lactone | erythrono-1,4-lact

Storage

Room temperature

Shipped In

Normal

Overview

Purity > 97%
A chiral synthon used to create analogs of certain natural products.

Specifications

Synonyms

3, 4-Dihydroxyoxolan-2-onato(3-) | MFCD00077763 | s11960 | Sedotussin (TN) | Q27159785 | SCHEMBL818248 | Carbamazepine10, 11-Epoxide | Rel-(3R, 4R)-3, 4-dihydroxydihydrofuran-2(3H)-one | Erythronic acid g-lactone | d-erythrono-1, 4-lactone | erythrono-1, 4-lact

Specifications & Purity

≥98%(GC)

Storage

Room temperature

Shipped In

Normal

Purity

≥98%(GC)

Names and Identifiers

• Pubchem Sid: 504763621
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763621
• Canonical Smiles: C1C(C(C(=O)O1)O)O
• IUPAC Name: (3R,4R)-3,4-dihydroxyoxolan-2-one
• InChIKey: SGMJBNSHAZVGMC-PWNYCUMCSA-N
• INCHI: 1S/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3-/m1/s1
• Isomeric SMILES: C1[C@H]([C@H](C(=O)O1)O)O
• WGK Germany: 3
• Molecular Weight: 118.09
• Beilstein: 81073
• Reaxy-Rn: 1281539
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1281539&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Lactones
      • Subclass Gamma butyrolactones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Lactones
• Subclass: Gamma butyrolactones
• Intermediate Tree Nodes: Not available
• Direct Parent: Gamma butyrolactones
• Alternative Parents: Tetrahydrofurans Secondary alcohols Carboxylic acid esters 1,2-diols Oxacyclic compounds Monocarboxylic acids and derivatives Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Gamma butyrolactone - Tetrahydrofuran - Secondary alcohol - Carboxylic acid ester - 1,2-diol - Oxacycle - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Alcohol - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as gamma butyrolactones. These are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
• 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

Associated Targets(non-human)

Trypanosoma brucei (78846 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Plasmodium falciparum (966862 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Leishmania donovani (89745 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Trypanosoma cruzi (99888 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water, and methanol.
• Specific Rotation[α]: -71° (C=1,H2O)
• Melt Point(°C): 103 °C
• Molecular Weight: 118.090 g/mol
• XLogP3: -1.300
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 118.027 Da
• Monoisotopic Mass: 118.027 Da
• Topological Polar Surface Area: 66.800 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 111.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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

References

1. Shuqi Wang, Yingshuang Hui, Yulu Zhan, Lou Gao, Yahong Zhang, Yi Tang.  (2023)  Sugars as Emerging Hydrogen Donors in the Synthesis of Alditol via Catalytic Transfer Hydrogenation.  ChemCatChem,  15  (18): (e202300213).  [PMID:] [10.1002/cctc.202300213]