583-50-6 , D-赤藓糖,
D-Erythrose,
CAS:583-50-6
C4H8O4 / 120.1
MFCD00006970
Erythrose is a sugar that is used in the biosynthesis of other sugars, such as ribose and D-erythrose. It is also an intermediate in the pentose phosphate pathway for the production of NADPH. Erythrose can be converted to erythritol by reductase enzymes, which are necessary for the synthesis of DNA. The enzyme erythrose reductase has been shown to act on wild-type strains. Erythrose reduces d-erythrose to erythritol, which inhibits polymerase chain reactions by blocking transcription and replication of DNA. Erythrose has also been shown to have inhibitory properties against Toll-like receptor signaling pathways, which may be due to its ability to reduce reactive oxygen species (ROS) and hydrogen peroxide levels in cells.
D-Erythrose is an antitumor agent. D-Erythrose inhibits tumor growth in mice (in vivo). It is used to study the mechanisms of organic micro spherule formation and Maillard (glycation) reactions. D-erythrose significantly reduced the weight of the intraperitoneal tumor by 69.1%, markedly inhibited the development of ascites and increased tumor cell apoptosis, without any observed toxic effects. D-erythrose possesses antitumor activity against colon cancer.
Title: D-Erythrose
CAS Registry Number: 583-50-6
CAS Name: (2R,3R)-2,3,4-Trihydroxybutanal
Molecular Formula: C4H8O4
Molecular Weight: 120.10
Percent Composition: C 40.00%, H 6.71%, O 53.29%
Literature References: From calcium D-arabonate by oxidation with H2O2: Ruff, Ber. 32, 3674 (1899); 33, 1799 (1900). From D-glucose: Perlin, Methods Carbohydr. Chem. 1 (Academic Press, New York, 1962) p 64. Synthesis of DL-erythrose: Sonogashira, Nakagawa, Bull. Chem. Soc. Jpn. 45, 2616 (1972).
Properties: Syrup. Shows mutarotation. [a]D20 +1° ® -14.5° (3 days, c = 11). Sol in water. Slowly reduces cold Fehling's soln. Sodium amalgam reduces it to natural, inactive erythritol. No aldehyde reaction with benzenesulfhydroxamic acid. Not fermented by yeast.
Optical Rotation: [a]D20 +1° ® -14.5° (3 days, c = 11)
Derivative Type: Phenylosazone
Molecular Formula: C16H18N4O2
Molecular Weight: 298.34
Percent Composition: C 64.41%, H 6.08%, N 18.78%, O 10.73%
Properties: mp 164°.
Melting point: mp 164°
CAS Number | 583-50-6 |
Product Name | D-Erythrose |
IUPAC Name | (2R,3R)-2,3,4-trihydroxybutanal |
Molecular Formula | C4H8O4 |
Molecular Weight | 120.1 g/mol |
InChI | InChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h1,3-4,6-8H,2H2/t3-,4+/m0/s1 |
InChI Key | YTBSYETUWUMLBZ-IUYQGCFVSA-N |
SMILES | C(C(C(C=O)O)O)O |
Solubility | Soluble in DMSO |
Synonyms | 2,3,4-trihydroxybutanal, D-threose, erythrose, erythrose, (R*,S*)-isomer, erythrose, (R-(R*,S*))-isomer, erythrose, (S-(R*,S*))-isomer, L-threose, threose |
Canonical SMILES | C(C(C(C=O)O)O)O |
Isomeric SMILES | C([C@H]([C@H](C=O)O)O)O |
CAS No: 583-50-6 MDL No: MFCD00006970 Chemical Formula: C4H8O4 Molecular Weight: 120.1 | In Stock. |
References: 1. Benov L, Fridovichi L, J. Biol. Chem. 1998, 273 (40), p25741-257442. Shah RH, J. Carbohydr. Chem. 1986, Vol5, No1, p139-146 |
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