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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-12 21:20:02 UTC
Update Date2020-02-26 21:24:38 UTC
HMDB IDHMDB0003453
Secondary Accession Numbers
  • HMDB03453
Metabolite Identification
Common Name3-Hydroxypropanal
Description3-Hydroxypropanal is a broad-spectrum antimicrobial substance termed reuterin produced by Lactobacillus reuteri. L. reuteri resides in the gastrointestinal tract of healthy humans and animals, and is believed to. function as a symbiont in the enteric ecosystem. Synthesis of such an antimicrobial substance by an enteric resident raises a number of interesting questions and possibilities as to the role these residents may play in the health of the host. (PMID 3245697 ). In vivo, glycerol is converted in one enzymatic step into 3-Hydroxypropanal. The 3-Hydroxypropanal -producing Lactobacillus reuteri is used as a probiotic in the health care of humans and animals. 3-Hydroxypropanal forms, together with Hydroxypropanal-hydrate and Hydroxypropanal-dimer, a dynamic, multi-component system (Hydroxypropanal system) used in food preservation, as a precursor for many modern chemicals such as acrolein, acrylic acid, and 1,3-propanediol (1,3-PDO), and for polymer production. 3-Hydroxypropanal can be obtained both through traditional chemistry and bacterial fermentation. To date, 3-HPA has been produced from petrochemical resources as an intermediate in 1,3-PDO production. The biotechnological production of 3-Hydroxypropanal from renewable resources is desirable both for use of 3-Hydroxypropanal in foods and for the production of bulk chemicals. The main challenge will be the efficient production and recovery of pure 3-Hydroxypropanal. (PMID 14669058 ).
Structure
Data?1582752278
Synonyms
ValueSource
3-HydroxypropionaldehydeHMDB, MeSH
3-oxo-1-PropanolHMDB
b-HydroxypropanalHMDB
b-HydroxypropionaldehydeHMDB
beta-HydroxypropanalHMDB
beta-HydroxypropionaldehydeHMDB, MeSH
HydracroleinHMDB
ReuterinHMDB, MeSH
3-HPAMeSH, HMDB
Chemical FormulaC3H6O2
Average Molecular Weight74.0785
Monoisotopic Molecular Weight74.036779436
IUPAC Name3-hydroxypropanal
Traditional Nameβ-hydroxypropionaldehyde
CAS Registry Number2134-29-4
SMILES
OCCC=O
InChI Identifier
InChI=1S/C3H6O2/c4-2-1-3-5/h2,5H,1,3H2
InChI KeyAKXKFZDCRYJKTF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlpha-hydrogen aldehydes
Alternative Parents
Substituents
  • Alpha-hydrogen aldehyde
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility645 g/LALOGPS
logP10(-0.74) g/LALOGPS
logP10(-0.96) g/LChemAxon
logS10(0.94) g/LALOGPS
pKa (Strongest Acidic)13.42ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity18.12 m³·mol⁻¹ChemAxon
Polarizability7.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+112.16531661259
DarkChem[M-H]-105.32331661259
DeepCCS[M+H]+120.11730932474
DeepCCS[M-H]-118.23330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-HydroxypropanalOCCC=O1544.2Standard polar33892256
3-HydroxypropanalOCCC=O648.4Standard non polar33892256
3-HydroxypropanalOCCC=O732.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxypropanal,1TMS,isomer #1C[Si](C)(C)OCCC=O944.9Semi standard non polar33892256
3-Hydroxypropanal,1TMS,isomer #2C[Si](C)(C)OC=CCO983.1Semi standard non polar33892256
3-Hydroxypropanal,2TMS,isomer #1C[Si](C)(C)OC=CCO[Si](C)(C)C1105.5Semi standard non polar33892256
3-Hydroxypropanal,2TMS,isomer #1C[Si](C)(C)OC=CCO[Si](C)(C)C1046.5Standard non polar33892256
3-Hydroxypropanal,2TMS,isomer #1C[Si](C)(C)OC=CCO[Si](C)(C)C1076.4Standard polar33892256
3-Hydroxypropanal,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCC=O1165.5Semi standard non polar33892256
3-Hydroxypropanal,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC=CCO1194.7Semi standard non polar33892256
3-Hydroxypropanal,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCO[Si](C)(C)C(C)(C)C1511.0Semi standard non polar33892256
3-Hydroxypropanal,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCO[Si](C)(C)C(C)(C)C1504.4Standard non polar33892256
3-Hydroxypropanal,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC=CCO[Si](C)(C)C(C)(C)C1391.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxypropanal GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9000000000-6f0de04be07974a052bd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxypropanal GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9300000000-044493864a3d344227bf2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxypropanal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropanal 10V, Positive-QTOFsplash10-056r-9000000000-b527dd76b295599a67072017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropanal 20V, Positive-QTOFsplash10-0a4i-9000000000-5d755fc67c397e2dd6212017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropanal 40V, Positive-QTOFsplash10-0a70-9000000000-54f403409b830f57b5892017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropanal 10V, Negative-QTOFsplash10-00di-9000000000-c121e90d5362a1780d7c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropanal 20V, Negative-QTOFsplash10-00dl-9000000000-2dc320e96b74616f40eb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropanal 40V, Negative-QTOFsplash10-0006-9000000000-0021ce0ee9221943ac402017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropanal 10V, Positive-QTOFsplash10-0a4i-9000000000-46f5a128789cb1a670a22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropanal 20V, Positive-QTOFsplash10-0a4i-9000000000-f9cf01f57aa08ed9654e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropanal 40V, Positive-QTOFsplash10-052r-9000000000-ed02d307841f6070f7ea2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropanal 10V, Negative-QTOFsplash10-00di-9000000000-93afe7a35357d19abf662021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropanal 20V, Negative-QTOFsplash10-0a4i-9000000000-c17ad0c9c3a8a7d2783c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxypropanal 40V, Negative-QTOFsplash10-052f-9000000000-68a03885b61bc7330d492021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023176
KNApSAcK IDNot Available
Chemspider ID67601
KEGG Compound IDC00969
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkReuterin
METLIN ID6935
PubChem Compound75049
PDB IDNot Available
ChEBI ID17871
Food Biomarker OntologyNot Available
VMH ID3HPPNL
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceLu, Shunfeng; Wang, Shiliang; Peng, Bin; Qin, Yanhuang; Zhou, Zhiquan; Wu, Xiuxiang. Process for preparation of 3-hydroxypropanal and 1,3-propanediol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 10 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Olivares M, Diaz-Ropero MP, Martin R, Rodriguez JM, Xaus J: Antimicrobial potential of four Lactobacillus strains isolated from breast milk. J Appl Microbiol. 2006 Jul;101(1):72-9. [PubMed:16834593 ]
  2. Talarico TL, Casas IA, Chung TC, Dobrogosz WJ: Production and isolation of reuterin, a growth inhibitor produced by Lactobacillus reuteri. Antimicrob Agents Chemother. 1988 Dec;32(12):1854-8. [PubMed:3245697 ]
  3. Vollenweider S, Lacroix C: 3-hydroxypropionaldehyde: applications and perspectives of biotechnological production. Appl Microbiol Biotechnol. 2004 Mar;64(1):16-27. Epub 2003 Dec 11. [PubMed:14669058 ]