462233
D-Galactal
95%
Synonym(s):
1,5-Anhydro-2-deoxy-D-lyxo-hex-1-enitol
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About This Item
Empirical Formula (Hill Notation):
C6H10O4
CAS Number:
Molecular Weight:
146.14
Beilstein:
81690
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.22
Assay
95%
optical activity
[α]22/D −21.5°, c = 1.2 in methanol
mp
99-103 °C (lit.)
storage temp.
2-8°C
SMILES string
OC[C@H]1OC=C[C@@H](O)[C@H]1O
InChI
1S/C6H10O4/c7-3-5-6(9)4(8)1-2-10-5/h1-2,4-9H,3H2/t4-,5-,6-/m1/s1
InChI key
YVECGMZCTULTIS-HSUXUTPPSA-N
Application
Important building block for both solution- and solid-phase synthesis of oligosaccharides.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Comparison of the beta-galactosidase conformations induced by D-galactal and by magnesium ions.
O M Viratelle et al.
Biochemistry, 19(18), 4143-4149 (1980-09-02)
W Weiser et al.
Archives of biochemistry and biophysics, 292(2), 493-498 (1992-02-01)
Green coffee bean alpha-galactosidase was found to catalyze the hydration of D-galactal and (Z)-3,7-anhydro-1,2-dideoxy-D-galacto-oct-2-enitol (D-galacto-octenitol), each a known substrate for beta-galactosidase. The hydration of D-galactal by the alpha-galactosidase in D2O yielded 2-deoxy-2(S)-D-[2-2H]galactose; the hydration of D-[2-2H]galacto-octenitol in H2O yielded 1,2-dideoxy-2(R)-D-[2-2H]galactooct-3-ulose.
Francesca Leonelli et al.
Carbohydrate research, 343(7), 1133-1141 (2008-04-04)
The synthesis of new 2-phosphono-alpha-D-glycoside derivatives by stereoselective oxa-Michael addition to an enone derived from D-galactal and containing a phosphonate group is described. Retro-Michael reactions were prevented by tandem acetylation to trap the unstable enolic intermediates. The stereochemistry of the
L Kiss et al.
Carbohydrate research, 291, 43-52 (1996-09-23)
C-(2-Deoxy-D-lyxo-hex-1-enopyranosyl)formamide was prepared from acetylated C-(beta-D-galactopyranosyl)formamide by a radical-mediated bromination-zinc/N-methylimidazole-induced reductive elimination-Zemplén deacetylation reaction sequence. The preparation of acetylated 5-(2-deoxy-D-lyxo-hex-1-enopyranosyl)tetrazole was improved. Methyl C-(2-deoxy-D-lyxo-hex-1-enopyranosyl)formimidate was transformed by benzylamine into N-benzyl-C-(2-deoxy-D-lyxo-hex-1-enopyranosyl)formamidine and, after hydrolysis to methyl C-(2-deoxy-D-lyxo-hex-1-enopyranosyl)formate, into N-benzyl-C-(2-deoxy-D-lyxo-hex-1-enopyranosyl)formamide. A series
Affinity labelling of beta-D-galactosidase from Escherichia coli with D-[6-(3)H]-galactal.
G Kurz et al.
Carbohydrate research, 93(1), C14-C20 (1981-06-16)
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