[ CAS No. 497-09-6 ] {[proInfo.proName]}

Name: 497-09-6|(S)-2,3-Dihydroxypropanal|90% in H2O
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SKU: A148763
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Quality Control of [ 497-09-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 497-09-6 ]

Product Details of [ 497-09-6 ]

CAS No. :	497-09-6	MDL No. :	MFCD00006971
Formula :	C₃H₆O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MNQZXJOMYWMBOU-GSVOUGTGSA-N
M.W :	90.08	Pubchem ID :	439723
Synonyms :

Safety of [ 497-09-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 497-09-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 497-09-6 ]
Downstream synthetic route of [ 497-09-6 ]

[ 497-09-6 ] Synthesis Path-Upstream 1~2

1
[ 497-09-6 ]
[ 87-79-6 ]

Yield	Reaction Conditions	Operation in experiment
54%	With FAD; Staphylococcus carnosus D-fructose 1,6-bisphosphate aldolase; Streptococcus pneumonia glycerol phosphate oxidase In water-d2 at 30℃; for 22 h; Enzymatic reaction	General procedure: To a solution of DL-glycerol 3-phosphate magnesium salt (548.78 mg, 2.4 mmol) in 6.86 mL ddH₂O was added D-glyceraldehyde (or L-glyceraldehyde) (2 mL, 0.5 M, 1.0 mmol) at pH 7.0, glycerol phosphate oxidase saturated with FAD (final concentration 0.2 mg/mL), catalase (1000 U, 1.18 μL) and aldolase (final concentration 0.5 mg/mL). ddH2O was added to bring the total volume to 10 mL if necessary. The reaction mixture was shaken at 30 °C for 22 h and the reaction was monitored by TLC (developed by nBuOH/AcOH/H₂O 2/1/1 (v/v/v) and stained with anisaldehyde sugar stain). The pH was then adjusted to pH ~5 with 6 N HCl and 11 μL acid phosphatase (18 U) was added and the mixture was shaken at 37 °C for 24 h. After cooling to rt., the pH was adjusted to 7.0 with 1 N NaOH and the mixture was diluted with methanol. The solution was filtered through Celite and washed with methanol. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (EtOAc/iPrOH/H₂O 9/3/1 (v/v/v)) to afford a pale yellow syrup which was further purified by Bio gel P-2 column. The mixture of monosaccharides could be isolated by Ca²⁺ exchange resin column. The purification process using P-2 column or Ca²⁺ exchange resin column was performed with the same procedure we previously used.
28%	Stage #1: With glycerol phosphate oxidase; recombinant D-fructose 1,6-bisphosphate aldolase from Staphylococcus carnosus; catalase In water at 20℃; for 22 h; Enzymatic reaction Stage #2: With hydrogenchloride; acid phosphatase from sweet potato In water at 37℃; for 24 h; Enzymatic reaction	To a solution of DL-glycerol 3-phosphate magnesium salt (548.78 mg, 2.4 mmol) in 6.86 mL ddH₂O were added D-glyceraldehyde (or L-glyceraldehyde) (2 mL, 0.5 M, 1.0 mmol) at pH 7.0, glycerol phosphate oxidase (70 U, 2 mg), catalase (1000 U, 1.18 μL), and FruA_S.car (final concentration 0.5 mg/mL). ddH₂O was added to bring the total volume to 10 mL if necessary. The mixture was shaken at rt for 22 h and the reaction was monitored by TLC (developed by nBuOH/AcOH/H₂O: 2/1/1 (v/v/v) and stained with anisaldehyde sugar stain). The pH was then adjusted to pH .similar.5 with 6 M HCl and 11 μL acid phosphatase (18 U) was added and the mixture was shaken at 37 °C for 24 h. After cooling to rt, the pH was adjusted to 7.0 with 1 M NaOH and the mixture was diluted with methanol. The solution was filtered through Celite and washed with methanol. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (EtOAc/iPrOH/H₂O: 9/3/1 (v/v/v)) to afford a pale yellow syrup which was further purified by Bio gel P-2 column. After purification, 108 mg d-fructose (60percent yield based on d-glyceraldehyde) and 50.9 mg l-sorbose (28percent yield based on l-glyceraldehyde) were obtained, respectively.

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 3, p. 504 - 507
[2] Carbohydrate Research, 2012, vol. 357, p. 143 - 146

2
[ 497-09-6 ]
[ 96-26-4 ]
[ 87-79-6 ]

Reference： [1] Chemistry - A European Journal, 2011, vol. 17, # 9, p. 2623 - 2632

[ 497-09-6 ] Synthesis Path-Downstream 1~80

1
[ 84984-53-2 ]
[ 497-09-6 ]

Reference： [1]Pflugers Archiv fur die gesamte Physiologie des Menschen und der Tiere,1932,vol. 230,p. 529

2
[ 20703-66-6 ]
[ 497-09-6 ]

Reference： [1]Biochemische Zeitschrift,1910,vol. 27,p. 345

3
[ 5328-37-0 ]
[ 497-09-6 ]

Reference： [1]Canadian Journal of Chemistry,1955,vol. 33,p. 1216,1219
Canadian Journal of Chemistry,1956,vol. 34,p. 541,549

4
[ 87-79-6 ]
[ 497-09-6 ]

Reference： [1]Canadian Journal of Chemistry,1956,vol. 34,p. 85,1848

5
[ 497-09-6 ]
[ 126-81-8 ]
2-(2-hydroxymethyl-6,6-dimethyl-4-oxo-2,3,4,5,6,7-hexahydro-benzofuran-3-yl)-5,5-dimethyl-cyclohexane-1,3-dione [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 761,764

6
[ 5328-37-0 ]
[ 546-67-8 ]
[ 64-19-7 ]
[ 497-09-6 ]

Reference： [1]Canadian Journal of Chemistry,1955,vol. 33,p. 1216,1219
Canadian Journal of Chemistry,1956,vol. 34,p. 541,549

7
[ 497-09-6 ]
[ 119-26-6 ]
[ 111955-85-2 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 761,764

8
[ 4306-35-8 ]
[ 497-09-6 ]

Reference： [1]Journal of the American Chemical Society,1950,vol. 72,p. 2404

9
[ 57-04-5 ]
[ 497-09-6 ]
[ 57-48-7 ]

Reference： [1]Journal of the American Chemical Society,1994,vol. 116,p. 558 - 561
[2]Journal of Organic Chemistry,1995,vol. 60,p. 4294 - 4295

10
[ 57-04-5 ]
[ 497-09-6 ]
[ 133007-25-7 ]
[ 19456-80-5 ]

Reference： [1]Angewandte Chemie,1991,vol. 103,p. 596 - 599
[2]Angewandte Chemie,1991,vol. 103,p. 596 - 599

11
[ 497-09-6 ]
[ 488-69-7 ]
[ 49594-02-7 ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 8103 - 8106

12
[ 497-09-6 ]
[ 96-26-4 ]
[ 20880-92-6 ]

Reference： [1]Carbohydrate Research,1982,vol. 107,p. 137 - 141

13
[ 497-09-6 ]
[ 52-89-1 ]
[ 124617-03-4 ]

Reference： [1]Carbohydrate Research,1989,vol. 187,p. 223 - 238

14
[ 497-09-6 ]
[ 113-24-6 ]
(2R,4R,5S)-2,4,5-Trihydroxy-tetrahydro-pyran-2-carboxylic acid; compound with ammonia [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1993,vol. 115,p. 413 - 421

15
[ 497-09-6 ]
[ 57-60-3 ]
(4R,5S)-4,5,6-Trihydroxy-2-oxo-hexanoic acid; compound with ammonia [ No CAS ]
(4S,5S)-4,5,6-Trihydroxy-2-oxo-hexanoic acid; compound with ammonia [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1993,vol. 4,p. 1165 - 1168

16
[ 497-09-6 ]
C₃H₈NO₅P^(2-) [ No CAS ]
1-Desoxy-L-fructose-1-phosphoramidat [ No CAS ]