D-Galactose

HCID 6036

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Basic information

CAS
10257-28-0
Standard SMILES
OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O
InChIKey
WQZGKKKJIJFFOK-SVZMEOIVSA-N
Molecular formula
C6H12O6
Average molar mass
180.16 g/mol
Monoisotopic mass
180.0633881

Overview

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.

Names & identifiers

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

Names & synonyms

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

Database identifiers

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

Properties

Computed structural propertiesFilling in

XLogP
-2.6
Topological polar surface area
110 Ų
Hydrogen bond donors
5
Hydrogen bond acceptors
6
Rotatable bonds
1
Heavy atoms
12

Experimental & physicochemical properties

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 items

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]

Safety & regulation

GHS classification

GHS Classification · 6 items

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)

Hazard information

Regulatory Information · 3 items

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 item

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 items

Not Classified

Eye Irrit. 2A (100%)

Toxicology

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

Chemistry & industry

Pharmacology

ATC Code · 2 items

V - Various

QV - Various

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

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 item

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 item

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.

Uses & manufacturing

Uses · 3 items

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 items

D-Galactose: ACTIVE

Galactose: ACTIVE

Suppliers22 total

湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
广州佳途科技股份有限公司81960175 18933936954 · [email protected]
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]

Related reactions

7 records

Compound notes

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