基本情報
- 標準SMILES
OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O- InChIKey
WQZGKKKJIJFFOK-SVZMEOIVSA-N- 分子式
- C6H12O6
- 平均分子量
- 180.16 g/mol
- 単同位体質量
- 180.0633881
概要
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.
名称と識別子
- 優先名称
- D-Galactose
- IUPAC
- (3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
名称と別名
名称をさらに表示
データベース識別子
- 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
物性
構造計算による物性
- XLogP
- -2.6
- 極性表面積
- 110 Ų
- 水素結合供与体数
- 5
- 水素結合受容体数
- 6
- 回転可能結合数
- 1
- 重原子数
- 12
- 形式電荷
- 0
- 複雑度
- 151
実験および物理化学的性質
Collision Cross Section
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]
安全と法規制
GHS分類
GHS Classification
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)
危険有害性情報
Regulatory Information
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
Hazards Summary
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
Not Classified
Eye Irrit. 2A (100%)
毒性情報
化学と産業
薬理情報
ATC Code
V - Various
QV - Various
Pharmacodynamics
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
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.
Metabolism/Metabolites
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
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.
用途と製造
Uses
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
D-Galactose: ACTIVE
Galactose: ACTIVE
関連反応
関連ノート
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