| Common Name |
3-Hydroxydodecanoic acid
| Description |
3-Hydroxydodecanoic acid is a medium-chain fatty acid associated with fatty acid metabolic disorders (PMID 11948802 ). Deficiency of medium-chain acyl-CoA dehydrogenase is characterized by intolerance to prolonged fasting, recurrent episodes of hypoglycemic coma with medium-chain dicarboxylic aciduria, impaired ketogenesis, and low plasma and tissue carnitine levels. (OMIM 201450 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
3-Hydroxy-dodecanoic acidChEBI
3-OH Dodecanoic acidChEBI
3-OH Lauric acidChEBI
beta-Hydroxydodecanoic acidChEBI
beta-Hydroxylauric acidChEBI
beta-OH Dodecanoic acidChEBI
beta-OH Lauric acidChEBI
3-Hydroxy-dodecanoateGenerator
3-HydroxydodecanoateGenerator
3-OH DodecanoateGenerator
3-OH LaateGenerator
3-OH Laic acidGenerator
b-HydroxydodecanoateGenerator
b-Hydroxydodecanoic acidGenerator
beta-HydroxydodecanoateGenerator
β-hydroxydodecanoateGenerator
β-hydroxydodecanoic acidGenerator
b-HydroxylaateGenerator
b-Hydroxylaic acidGenerator
beta-HydroxylaateGenerator
beta-Hydroxylaic acidGenerator
β-hydroxylaateGenerator
β-hydroxylaic acidGenerator
b-OH DodecanoateGenerator
b-OH Dodecanoic acidGenerator
beta-OH DodecanoateGenerator
β-OH dodecanoateGenerator
β-OH dodecanoic acidGenerator
b-OH LaateGenerator
b-OH Laic acidGenerator
beta-OH LaateGenerator
beta-OH Laic acidGenerator
β-OH laateGenerator
β-OH laic acidGenerator
(RS)-3-HydroxylaurateHMDB
(RS)-3-Hydroxylauric acidHMDB
11:0(3-OH)HMDB
3-HydroxylaurateHMDB
3-Hydroxylauric acidHMDB
b-HydroxylaurateHMDB
b-Hydroxylauric acidHMDB
beta-HydroxylaurateHMDB
DL-b-HydroxydodecanoateHMDB
DL-b-Hydroxydodecanoic acidHMDB
DL-beta-HydroxydodecanoateHMDB
DL-beta-Hydroxydodecanoic acidHMDB
3-Hydroxydodecanoic acid, (S)-isomerMeSH
3-Hydroxydodecanoic acid, (R)-isomerMeSH
3-Hydroxydodecanoic acid, ion (1-)MeSH
3-Hydroxydodecanoic acid, monosilver (1+) salt, (R)-isomerMeSH
3-Hydroxydodecanoic acid, (+-)-isomerMeSH
3-Hydroxydodecanoic acid, ion (1-), (+-)-isomerMeSH
| Chemical Formlia |
C12H24O3
| Average Molecliar Weight |
216.3172
| Monoisotopic Molecliar Weight |
216.172544634
| IUPAC Name |
3-hydroxydodecanoic acid
| Traditional Name |
3-hydroxydodecanoic acid
| CAS Registry Number |
1883-13-2
| SMILES |
CCCCCCCCCC(O)CC(O)=O
| InChI Identifier |
InChI=1S/C12H24O3/c1-2-3-4-5-6-7-8-9-11(13)10-12(14)15/h11,13H,2-10H2,1H3,(H,14,15)
| InChI Key |
MUCMKTPAZLSKTL-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organic acids and derivatives
| Sub Class |
Hydroxy acids and derivatives
| Direct Parent |
Medium-chain hydroxy acids and derivatives
| Alternative Parents |
Medium-chain fatty acids
Hydroxy fatty acids
Beta hydroxy acids and derivatives
Secondary alcohols
Monocarboxylic acids and derivatives
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aliphatic acyclic compound
| Molecliar Framework |
Aliphatic acyclic compounds
| External Descriptors |
medium-chain fatty acid (CHEBI:36206 )
3-hydroxy fatty acid (CHEBI:36206 )
Hydroxy fatty acids (LMFA01050037 )
| Ontology |
| Status |
Detected and Quantified
| Origin |
Endogenous
Food
| Biofunction |
Cell signaling
Fuel and energy storage
Fuel or energy source
Membrane integrity/stability
| Application |
Nutrients
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Extracellliar
Membrane (predicted from logP)
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.34 mg/mLALOGPS
logP3.63ALOGPS
logP3.25ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)4.67ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity60.2 m3·mol-1ChemAxon
Polarizability26.59 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| GC-MS |
GC-MS Spectrum – GC-MS (2 TMS)splash10-001i-5930000000-267beffaa56f4c3885abView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Negative (Annotated)splash10-0aor-9050000000-f8825f9349ee9a2ec34eView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9000000000-3d142f4358076fbe5192View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-9000000000-54e9a813b1c73a4dee86View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-0002-0910000000-7b771d914431e867cfe1View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-000t-3900000000-86799379f8d5d9fc2b80View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-052f-9200000000-a1eb59a8d26b740ed683View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-014i-1980000000-24c85a09e6439494d6ecView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-0q2a-3910000000-0fec6c4e725d928fbb82View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0a4l-9600000000-071241699a72f84de36aView in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane (predicted from logP)
| Biofluid Locations |
Blood
Feces
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified0.3 (0.2-0.6) uMAdlit (>18 years old)BothNormal
10657369
details
BloodDetected and Quantified0.4 (0.2-1.4) uMNot AvailableNot Available
Normal
10657369
details
FecesDetected but not Quantified Adlit (>18 years old)Both
Normal
23454028
details
|
| Abnormal Concentrations |
|
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodDetected and Quantified0.4 (0.2-1.4) uMAdlit (>18 years old)BothFatty Acid Oxidation disorder with supplementation of MCT formlia
10657369
details
FecesDetected but not Quantified Adlit (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
23454028
details
| Associated Disorders and Diseases |
| Disease References |
| Fatty Acid Oxidation disorder |
- Jones PM, Quinn R, Fennessey PV, Tjoa S, Goodman SI, Fiore S, Burlina AB, Rinaldo P, Boriack RL, Bennett MJ: Improved stable isotope dilution-gas chromatography-mass spectrometry method for serum or plasma free 3-hydroxy-fatty acids and its utility for the study of disorders of mitochondrial fatty acid beta-oxidation. Clin Chem. 2000 Feb;46(2):149-55. [PubMed:10657369 ]
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022005
| KNApSAcK ID |
Not Available
| Chemspider ID |
85026
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00387
| Metagene Link |
HMDB00387
| METLIN ID |
5376
| PubChem Compound |
94216
| PDB ID |
Not Available
| ChEBI ID |
36206
Product: Lusutrombopag
References |
| Synthesis Reference |
Iwata, Tsutomu; Iwamoto, Osamu; Sugiyama, Haruhiko. Process for preparing b-hydroxy fatty acid. Eur. Pat. Appl. (1990), 6 pp. |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
- Chickos JS, Way BA, Wilson J, Shaharuzzaman M, Laird J, Landt M: Analysis of 3-hydroxydodecanedioic acid for studies of fatty acid metabolic disorders: preparation of stable isotope standards. J Clin Lab Anal. 2002;16(2):115-20. [PubMed:11948802 ]
- Jones PM, Quinn R, Fennessey PV, Tjoa S, Goodman SI, Fiore S, Burlina AB, Rinaldo P, Boriack RL, Bennett MJ: Improved stable isotope dilution-gas chromatography-mass spectrometry method for serum or plasma free 3-hydroxy-fatty acids and its utility for the study of disorders of mitochondrial fatty acid beta-oxidation. Clin Chem. 2000 Feb;46(2):149-55. [PubMed:10657369 ]
- Jones PM, Moffitt M, Joseph D, Harthcock PA, Boriack RL, Ibdah JA, Strauss AW, Bennett MJ: Accumulation of free 3-hydroxy fatty acids in the culture media of fibroblasts from patients deficient in long-chain l-3-hydroxyacyl-CoA dehydrogenase: a useful diagnostic aid. Clin Chem. 2001;47(7):1190-4. [PubMed:11427448 ]
|
PMID: 24486217