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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:07 UTC
NP-MRD IDNP0000455
Secondary Accession NumbersNone
Natural Product Identification
Common Name5Z-Dodecenoic acid
Description5Z-Dodecenoic acid, also known as 5-dodecenoic acid or 5-dodecenoate, is a monounsaturated fatty acid that has a C12 chain as a backbone and a cis double bond at the C5 position. 5-Dodecenoic acid is a member of the class of compounds known as medium-chain fatty acids. Medium-chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Thus, 5-dodecenoic acid is considered to be a fatty acid lipid molecule. 5-Dodecenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Within the cell, 5-dodecenoic acid is primarily located in the cytoplasm and in the membrane (predicted from logP). It can also be found in the extracellular space. An increase of 5-dodecenoic acid in plasma is associated with acyl-CoA dehydrogenase deficiency disorders (PMID: 7586519 ). 5-Dodecenoic acid is an intermediate of unsaturated fatty acid oxidation.
Structure
Thumb
Synonyms
ValueSource
5Z-DodecenoateGenerator
cis-5-Dodecanoic acidHMDB
cis-5-DodecanoateHMDB
5-DodecenoateHMDB
(Z)-5-DodecenoateHMDB
(Z)-5-Dodecenoic acidHMDB
cis-5-DodecenoateHMDB
cis-5-Dodecenoic acidHMDB
5-Dodecenoic acid, (e)-isomerHMDB
(Z)-Dodec-5-enoic acidHMDB
(Z)-Dodec-5-enoateHMDB
5-Dodecenoic acidHMDB
FA(12:1(5Z))HMDB
LauroleinateHMDB
Chemical FormulaC12H22O2
Average Mass198.3019 Da
Monoisotopic Mass198.16198 Da
IUPAC Name(5Z)-dodec-5-enoic acid
Traditional Namecis-5-dodecenoic acid
CAS Registry Number2430-94-6
SMILES
CCCCCC\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C12H22O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h7-8H,2-6,9-11H2,1H3,(H,13,14)/b8-7-
InChI KeyIJBFSOLHRKELLR-FPLPWBNLSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aquilaria sinensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility9.12 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP4.76ALOGPS
logP4.12ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity59.8 m³·mol⁻¹ChemAxon
Polarizability24.53 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000529
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022097
KNApSAcK IDNot Available
Chemspider ID4471803
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5514
PubChem Compound5312378
PDB IDNot Available
ChEBI ID86595
Good Scents IDrw1587421
References
General References
  1. Onkenhout W, Venizelos V, van der Poel PF, van den Heuvel MP, Poorthuis BJ: Identification and quantification of intermediates of unsaturated fatty acid metabolism in plasma of patients with fatty acid oxidation disorders. Clin Chem. 1995 Oct;41(10):1467-74. [PubMed:7586519 ]
  2. Henry GE, Momin RA, Nair MG, Dewitt DL: Antioxidant and cyclooxygenase activities of fatty acids found in food. J Agric Food Chem. 2002 Apr 10;50(8):2231-4. doi: 10.1021/jf0114381. [PubMed:11929276 ]
  3. Yu H, Gild P, Pompe RS, Vetterlein MW, Ludwig TA, Soave A, Kolker M, Maurer V, Marks P, Becker A, Punke MA, Fisch M, Rink M, Dahlem R, Meyer CP: Anesthetic Technique (Spinal vs. General Anesthesia) in Holmium Laser Enucleation of the Prostate: Retrospective Analysis of Procedural and Functional Outcomes among 1,159 Patients. Urol Int. 2021 Aug 17:1-8. doi: 10.1159/000517542. [PubMed:34404060 ]
  4. Al Riyees L, Al Madani W, Firwana N, Balkhy HH, Ferwana M, Alkhudhayri A: Antibiotic Prophylaxis against Surgical Site Infection after Open Hernia Surgery: A Systematic Review and Meta-Analysis. Eur Surg Res. 2021 Aug 17:1-13. doi: 10.1159/000517404. [PubMed:34404046 ]
  5. Geer MJ, Foucar CE, Devata S, Benitez L, Perissinotti AJ, Marini BL, Bixby D: Clinical Availability of ATRA for Patients With Suspected Acute Promyelocytic Leukemia: Why Guidelines May Not Be Followed. J Natl Compr Canc Netw. 2021 Aug 17. pii: jnccn20455. doi: 10.6004/jnccn.2021.7013. [PubMed:34404029 ]
  6. Enwemeka CS, Bumah VV, Mokili JL: Pulsed blue light inactivates two strains of human coronavirus. J Photochem Photobiol B. 2021 Aug 8;222:112282. doi: 10.1016/j.jphotobiol.2021.112282. [PubMed:34404018 ]
  7. Wang Y, Liu X, Yu L, Hong X, Zhao J, Zhu J, Yuan J, Li W, Zhu X: Identification and analysis of novel microRNAs provide insights to reproductive capacity of the cultured Asian yellow pond turtle Mauremys mutica. Comp Biochem Physiol Part D Genomics Proteomics. 2021 Aug 8;40:100890. doi: 10.1016/j.cbd.2021.100890. [PubMed:34404014 ]
  8. Yang K, Li CY, An JP, Wang DR, Wang X, Wang CK, You CX: The C2H2-type zinc finger transcription factor MdZAT10 negatively regulates drought tolerance in apple. Plant Physiol Biochem. 2021 Aug 10;167:390-399. doi: 10.1016/j.plaphy.2021.08.014. [PubMed:34404010 ]
  9. Dai L, Yang H, Zhao X, Wang L: Identification of cis conformation natural rubber and proteins in Ficus altissima Blume latex. Plant Physiol Biochem. 2021 Aug 10;167:376-384. doi: 10.1016/j.plaphy.2021.08.015. [PubMed:34404008 ]
  10. Wang LJ, Gao X, Jia GX: Stomata and ROS changes during Botrytis elliptica infection in diploid and tetraploid Lilium rosthornii Diels. Plant Physiol Biochem. 2021 Aug 6;167:366-375. doi: 10.1016/j.plaphy.2021.08.008. [PubMed:34404007 ]
  11. Sawczuk R, Karpinska J, Filipowska D, Bajguz A, Hryniewicka M: Evaluation of total phenols content, anti-DPPH activity and the content of selected antioxidants in the honeybee drone brood homogenate. Food Chem. 2021 Aug 3;368:130745. doi: 10.1016/j.foodchem.2021.130745. [PubMed:34404004 ]