Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:07:09 UTC |
---|
Update date | 2020-09-17 15:42:24 UTC |
---|
Primary ID | FDB006453 |
---|
Secondary Accession Numbers | |
---|
Chemical Information |
---|
FooDB Name | Galactitol |
---|
Description | Galactitol or dulcitol is a sugar alcohol that is a metabolic breakdown product of galactose. Galactitol is an extremely weak basic (essentially neutral) compound (based on its pKa). Galactose is derived from lactose in food (such as dairy products). When lactose is broken down by the enzyme lactase it produces glucose and galactose. It is this galactose that is broken down to galactitol via a reaction catalyzed by aldose reductase. Galactitol has a slightly sweet taste. When present in sufficiently high levels, galactitol can act as a metabotoxin, a neurotoxin, and a hepatotoxin. A neurotoxin is a compound that disrupts or attacks neural cells and neural tissue. A hepatotoxin as a compound that disrupts or attacks liver tissue or liver cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of galactitol are associated with at least two inborn errors of metabolism, including galactosemia and galactosemia type II. Galactosemia is a rare genetic metabolic disorder that affects an individual's ability to metabolize the sugar galactose properly. Excess lactose consumption in individuals with galactose intolerance or galactosemia activates aldose reductase to produce galactitol, thus depleting NADPH and leading to lowered glutathione reductase activity. As a result, hydrogen peroxide or other free radicals accumulate causing serious oxidative damage to various cells and tissues. In individuals with galactosemia, the enzymes needed for the further metabolism of galactose (galactose-1-phosphate uridyltransferase) are severely diminished or missing entirely, leading to toxic levels of galactose 1-phosphate, galactitol, and galactonate. High levels of galactitol in infants are specifically associated with hepatomegaly (an enlarged liver), cirrhosis, renal failure, cataracts, vomiting, seizure, hypoglycemia, lethargy, brain damage, and ovarian failure. Outside of the human body, Galactitol has been detected, but not quantified in, several different foods, such as common buckwheats, winter squash, calabash, black walnuts, and peanuts. This could make galactitol a potential biomarker for the consumption of these foods. |
---|
CAS Number | 608-66-2 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
(2R,3S,4R,5S)-Hexane-1,2,3,4,5,6-hexol | ChEBI | D-Dulcitol | ChEBI | D-Galactitol | ChEBI | Dulcitol | ChEBI | Dulcose | ChEBI | Euonymit | ChEBI | L-Galactitol | ChEBI | Melampyrin | ChEBI | Melampyrit | ChEBI | Ambap5938 | HMDB | Dulcite | HMDB | Hexitol | HMDB | Melampyrite | HMDB | Melampyrum | HMDB | meso-Galactitol | HMDB | galacto-Hexitol | db_source | Meso-galactitol | HMDB |
|
---|
Predicted Properties | |
---|
Chemical Formula | C6H14O6 |
---|
IUPAC name | (2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol |
---|
InChI Identifier | InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6- |
---|
InChI Key | FBPFZTCFMRRESA-GUCUJZIJSA-N |
---|
Isomeric SMILES | OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO |
---|
Average Molecular Weight | 182.1718 |
---|
Monoisotopic Molecular Weight | 182.07903818 |
---|
Classification |
---|
Description | Belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organic oxygen compounds |
---|
Class | Organooxygen compounds |
---|
Sub Class | Carbohydrates and carbohydrate conjugates |
---|
Direct Parent | Sugar alcohols |
---|
Alternative Parents | |
---|
Substituents | - Sugar alcohol
- Monosaccharide
- Secondary alcohol
- Polyol
- Hydrocarbon derivative
- Primary alcohol
- Alcohol
- Aliphatic acyclic compound
|
---|
Molecular Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Physiological effect | Health effect: |
---|
Disposition | Route of exposure: Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Role | Indirect biological role: Biological role: Industrial application: |
---|
Physico-Chemical Properties - Experimental |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Solid | |
---|
Physical Description | Not Available | |
---|
Mass Composition | Not Available | |
---|
Melting Point | 189.5 oC | |
---|
Boiling Point | Not Available | |
---|
Experimental Water Solubility | 31 mg/mL at 15 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
---|
Experimental logP | -3.10 | HANSCH,C ET AL. (1995) |
---|
Experimental pKa | Not Available | |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | Not Available | |
---|
Spectroscopic UV Data | Not Available | |
---|
Density | Not Available | |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
GC-MS | Galactitol, non-derivatized, GC-MS Spectrum | splash10-014j-0941000000-61141f9f2ddc66e0b016 | Spectrum | GC-MS | Galactitol, 6 TMS, GC-MS Spectrum | splash10-0gb9-1983000000-0a0dafcfea843fbb3c72 | Spectrum | GC-MS | Galactitol, non-derivatized, GC-MS Spectrum | splash10-014j-0941000000-61141f9f2ddc66e0b016 | Spectrum | GC-MS | Galactitol, non-derivatized, GC-MS Spectrum | splash10-0gb9-1983000000-0a0dafcfea843fbb3c72 | Spectrum | Predicted GC-MS | Galactitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03k9-9400000000-7a0f08ea65cbca1920f5 | Spectrum | Predicted GC-MS | Galactitol, 6 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a6s-7141193000-dcd9245e12314ee0ced4 | Spectrum | Predicted GC-MS | Galactitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Galactitol, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated) | splash10-005a-5900000000-35da0de23de5b9170aed | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-0a4i-9000000000-552b84764ceb9b497a7e | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated) | splash10-052f-9000000000-dfb4eef021d94d514588 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive | splash10-0cdi-9200000000-864013c7cfca78751f1a | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive | splash10-052f-9000000000-d8bbc3d4a1c6c5aee49d | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive | splash10-0a4i-9000000000-d919d47fb365625ddad8 | Spectrum | MS/MS | LC-MS/MS Spectrum - QqQ 4V, negative | splash10-001i-0900000000-028ff289dc870279e218 | Spectrum | MS/MS | LC-MS/MS Spectrum - QqQ 8V, negative | splash10-001i-1900000000-a99ee988b2a1bbab9137 | Spectrum | MS/MS | LC-MS/MS Spectrum - QqQ 12V, negative | splash10-0uyr-6900000000-04315425478b660c8947 | Spectrum | MS/MS | LC-MS/MS Spectrum - QqQ 16V, negative | splash10-0kg9-9400000000-54350b0516f39f8c9b50 | Spectrum | MS/MS | LC-MS/MS Spectrum - QqQ 20V, negative | splash10-0abi-9100000000-b4cf2b00830b765d5dcb | Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 12V, negative | splash10-0089-9000000000-20463a683f8ab7aa9e4d | Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 12V, negative | splash10-0a4i-9000000000-5c4795e954d5c3e9b74e | Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 12V, negative | splash10-0udi-0900000000-43b7e571c1185de1e99b | Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 12V, negative | splash10-00di-9000000000-160eaf7ef39d08853738 | Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 12V, negative | splash10-0udi-3900000000-3114e2bfe0cdbc68be19 | Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 12V, negative | splash10-000j-9000000000-635a869063bea88c0091 | Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 12V, negative | splash10-0uk9-3900000000-2ecc694b3a9844ec3ee5 | Spectrum | MS/MS | LC-MS/MS Spectrum - Orbitrap 3V, negative | splash10-03di-0900000000-61d17fd37e0e3ac16e37 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-1900000000-8fd623cab2d92c8fe6bc | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-9100000000-6b1add40ffbd73109f44 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03dl-9000000000-91a1337ee99558df9b9b | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00su-8900000000-bab2cfe2d89285b51d20 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-06y6-9100000000-d4d223d12ef78c8ca224 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0btc-9000000000-9c0d6465be9cdfd04388 | Spectrum |
|
---|
NMR | |
---|
External Links |
---|
ChemSpider ID | 11357 |
---|
ChEMBL ID | CHEMBL1773904 |
---|
KEGG Compound ID | C01697 |
---|
Pubchem Compound ID | 11850 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | Not Available |
---|
DrugBank ID | Not Available |
---|
HMDB ID | HMDB00107 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | BVW44-V:BVW44-V |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | GALACTITOL |
---|
BIGG ID | 38183 |
---|
KNApSAcK ID | C00001160 |
---|
HET ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Galactitol |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | Not Available |
---|
Enzymes | Not Available |
---|
Pathways | |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Not Available |
---|
Files |
---|
MSDS | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
|
---|