D-Galactose

HCID 6036CAS 10257-28-0

Grundinformationen

Standard-SMILES
OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O
InChIKey
WQZGKKKJIJFFOK-SVZMEOIVSA-N
Summenformel
C6H12O6
Durchschnittliche Molmasse
180,16 g/mol
Monoisotopische Masse
180,0633881

Überblick

D-galactopyranose is a galactopyranose having D-configuration. It has a role as a mouse metabolite and an Escherichia coli metabolite. It is a D-galactose and a galactopyranose.

Namen und Bezeichner

Bevorzugter Name
D-Galactose
IUPAC
(3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

Namen und Synonyme

D-Galactopyranosegalactopyranosegalactopyranoside(3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrolGalactose, pureD-Gald-galactopyranosidecerebroseCHEBI:12936CHEBI:28061CHEBI:28260GAL
Weitere Namen anzeigen
D GalactoseNSC-8102SNFG:GalRefChem:7383Gal (SNFG)GlyTouCan:G68158BTCHEBI:37621DTXCID601437050

Datenbank-Bezeichner

CAS
10257-28-0、26566-61-0、59-23-4
PubChem CID
6036
DTXSID
DTXSID001015860
ChEMBL
CHEMBL195923、CHEMBL6067641
ChEBI
CHEBI:4139
EC Number
200-416-4、233-595-2
Nikkaji
J330.863D

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-2,6
Polarare Oberfläche (TPSA)
110 Ų
H-Brücken-Donoren
5
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
1
Schwere Atome
12

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Monosaccharides and Derivatives
CosmeticsCosmetic ingredients (Galactose) -> CIR (Cosmetic Ingredient Review)
SpringerMaterials PropertiesChemical shift
Vapor Pressure0.00000002 [mmHg]
Physical DescriptionWhite powder; [Sigma-Aldrich MSDS]
Collision Cross Section · 4 Einträge

142.39 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

142.1 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

141.9 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

136 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine]

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 100% (180 of 180) of all reports.

Not Classified

Aggregated GHS information provided per 180 reports by companies from 2 notifications to the ECHA C&L Inventory.

Warning

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: D-Galactose

D-Galactopyranose: Does not have an individual approval but may be used under an appropriate group standard

D-Galactose: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - D-Galactose: Human health tier I assessment
Hazards Summary · 1 Eintrag

Teratogenicity observed in rats at 55% of the diet; [Shepard's Catalog of Teratogenic Agents] Causes changes in motor activity, decreased cellular immune response, other liver changes, inflammation, other degenerative changes to brain and coverings, multiple enzyme effects, effects on lipids (including transport), changes in both tubules and glomeruli, and depressed renal function tests in acute subcutaneous studies of mice; [RTECS] May cause irritation; [Sigma-Aldrich MSDS]

Hazard Classes and Categories · 2 Einträge

Not Classified

Eye Irrit. 2A (100%)

Toxikologische Informationen

Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

V - Various

QV - Various

Protein BindingReadily accessible data regarding the protein binding of galactose is not available.
Pharmacodynamics · 1 Eintrag

Galactose is a naturally occurring monosaccharide that forms the disaccharide lactose when combined with glucose (another monosaccharide). Subsequently, when lactose or small amounts of free galactose found in various common dairy products (and other foods) are consumed, the hydrolysis of lactose to glucose and galactose occurs and galactose is itself further metabolized to generate glucose. Such glucose is, of course, ultimately relied upon and used as the primary metabolic fuel for humans in a variety of biological reactions. Conversely, however, the ways in which galactose is commonly used in therapeutic agents generally do not rely upon such pharmacodynamics, even though they ultimately remain the most important ways in which galactose exerts or elicits useful biological actions for the human body.

Mechanism of Action · 1 Eintrag

In the development of typhoid Ty21a live oral vaccine, the use of exogenous galactose is critical. When dealing with Salmonella typhimurium, it has been shown that rough strains with incomplete lipopolysaccharide (LPS) lacking O-specific side chains are much less virulent than smooth strains with complete LPS with O-specific side chains. Salmonella typhimurium gal E mutants used to produce the vaccine are effectively avirulent and highly protective but lack the specific UDP-galactose 4-epimerase enzyme which allows for the normal synthesis of UDP-galactose from UDP-glucose. The consequence of this mutant defect is that the gal E mutants can only generate incomplete LPS without O-specific antigen side chains, which are not capable enough as the complete LPS with O-specific side chains at generating an immunologic response. When exogenous galactose is added to the vaccine medium, however, it allows the mutants to generate UDP-galactose via galactose 1-phosphate. This ultimately allows the mutants to form smooth-type LPS with O-specific side chains. Regardless, the mutant's epimerase defect ultimately results in the accumulation of such intermediary products like galactose 1-phosphate and UDP-galactose, which consequently causes lysis of the mutant cells. The resultant vaccine is subsequently effective enough to elicit an immunologic response while the bacteriolysis prevents the mutant cells from regaining virulence under conditions where smooth type LPS similar to the active parental strain is synthesized. Galactose is also an essential element to the chemical structure of the commonly used laxative solution lactulose. Lactulose itself is a synthetic disaccharide that is made in parts from lactose, galactose, and various other sugars. It is poorly absorbed from the gastrointestinal tract and no enzyme capable of hydrolysis of lactulose is present in human gastrointestinal tissue. Oral doses of lactulose subsequently arrive at the colon largely unchanged. At the colon, lactulose is finally broken down predominantly to lactic acid, and also small amounts of formic and acetic acids by the action of colonic bacteria, which results in an increase in osmotic pressure and slight acidification of the colonic contents. This action consequently causes an increase in stool water content and softens the stool for a laxative effect.

Biological Half-LifeReadily accessible data regarding the half-life of galactose is not available.
Metabolism/Metabolites · 1 Eintrag

The primary pathway for galactose metabolism is called the Leloir pathway, so named after Luis Federico Leloir. The initial stage of this pathway is the conversion of beta-D-galactose to alpha-D-galactose by the enzyme galactose mutarotase (GALM). The pathway then performs the conversion of alpha-D-galactose to UDP-glucose by way of three principal enzymes and their reactions: galactokinase (GALK) phosphorylates alpha-D-galactose to galactose-1-phosphate (Gal-1-P); galactose-1-phosphate uridyltransferase (GALT) transfers a UMP group from UDP-glucose to Gal-1-P to form UDP-galactose; and finally, UDP galactose-4-epimerase (GALE) interconverts UDP-galactose and UDP-glucose, which completes the pathway.

Verwendung und Herstellung

Uses · 3 Einträge

CIR ingredient: Galactose

Component of many oligo- and polysaccharides in pectins, gums, and mucilages; Used in determination of hepatic function; [Merck Index]

Use (kg; approx.) in Germany (2009): >25

General Manufacturing Information · 2 Einträge

D-Galactose: ACTIVE

Galactose: ACTIVE

Zugehörige Reaktionen

7

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