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D-Galaktopyranose

D-Galactose

HCID 6036
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Grundinformationen

CAS
10257-28-0
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
Lokaler Name
D-Galaktopyranose
Englischer Name
D-(+)-Galactose
Summenformel
C6H12O6
Molmasse
180.16

Namen und Synonyme

D-Galactopyranosegalactopyranosegalactopyranoside(3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrolD-GalCHEBI:12936CHEBI:28061CHEBI:28260GALNSC-8102RefChem:7383GlyTouCan:G68158BT
Weitere Namen anzeigen
GALACTOSE(3R,4S,5R,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetraolNsc8102CEREBOSEGALACTOSE, D-(+)-Glucose impurity 11Lactulose impurity B(EP)-D-glucopyranosyl)-3-O-(&beta
CHEBI:37621DTXCID601437050G68158BT200-416-459-23-47IOF6H4H77Brain sugarCerebrose

Datenbank-Bezeichner

CAS
10257-28-0、26566-61-0、59-23-4
PubChem CID
6036
DTXSID

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
Formalladung
0
Komplexität
151

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]

Physikochemische Eigenschaften

Schmelzpunkt
168 · 168-170 °C(lit.)
Siedepunkt
410.8 · 410.8±45.0 °C(Predicted)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

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

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.

Zugehörige Reaktionen

7
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 7342
HRID 7342als Produktuspto-grants-2006_08
Reaktionsgleichung von HRID 19437
HRID 19437als Eduktuspto-grants-2010_06
Reaktionsgleichung von HRID 565147
HRID 565147als Eduktuspto-grants-2001_01
Reaktionsgleichung von HRID 1288645
HRID 1288645als Produktuspto-grants-1998_05
Reaktionsgleichung von HRID 1597767
HRID 1597767als Produktuspto-grants-1998_04
Reaktionsgleichung von HRID 1739613
HRID 1739613als Eduktuspto-grants-1999_10
Reaktionsgleichung von HRID 2172376
HRID 2172376als Produktuspto-grants-2015_06

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Weitere Aktionen
Neue NotizNeue ReaktionAnfrage stellen
DTXSID001015860
ChEMBL
CHEMBL195923、CHEMBL6067641
ChEBI
CHEBI:4139
EC Number
200-416-4、233-595-2
Nikkaji
J330.863D
Dichte
1.732 · 1.732±0.06 g/cm3(Predicted)
Löslichkeit
2 O: · H2O: 100 mg/mL
Aggregatzustand
powder
pka
12.12 · 12.12±0.70(Predicted)
CAS Datenbank
10257 · 10257-28-0(CAS DataBase Reference)
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

Sicherheitsdaten

F
3
wgk
3
RTECS-Nr.
LW5490000
safety_code
24/25
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.

Absorption, Distribution and Excretion · 4 Einträge

The absorption of galactose from the human jejunum was calculated to be 1.0 g per minute per 30 cm of the gut.

The primary route of elimination for galactose is hepatic.

It has been documented that galactose distributes in a volume equivalent to 40% of body weight.

In subjects with no liver disease, systemic galactose clearance was calculated to be 1.5 +/- 0.1 L/min.

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

Anwendungen

VerwendenDiagnostic aid (ultrasound contrast medium).

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

3,3',4,4',5',7-Hexahydro-2-phenyl-4H-chromen-4-on2-Acetamido-2-deoxy-D-galactitol6-Desoxy-L-β-galaktoseD-Glucose

Nachgelagerte Produkte

2,6-Anhydro-5-desoxy-D-arabino-hex-5-enitoltriacetat1,5-Anhydro-2-desoxy-D-lyxo-hex-1-enitolβ-D-Galaktosepentaacetat(-)-MaackiainAllyl-α-D-galactopyranoside

Ergänzende Hinweise

DefinitionA SUGAR found in lactose and many polysaccharides. It is an aldohexose, isomeric with glucose.