Record Information |
---|
Version | 1.0 |
---|
Created at | 2005-11-16 15:48:42 UTC |
---|
Updated at | 2021-08-19 23:58:07 UTC |
---|
NP-MRD ID | NP0000455 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | 5Z-Dodecenoic acid |
---|
Description | 5Z-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 | 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- |
---|
Synonyms | Value | Source |
---|
5Z-Dodecenoate | Generator | cis-5-Dodecanoic acid | HMDB | cis-5-Dodecanoate | HMDB | 5-Dodecenoate | HMDB | (Z)-5-Dodecenoate | HMDB | (Z)-5-Dodecenoic acid | HMDB | cis-5-Dodecenoate | HMDB | cis-5-Dodecenoic acid | HMDB | 5-Dodecenoic acid, (e)-isomer | HMDB | (Z)-Dodec-5-enoic acid | HMDB | (Z)-Dodec-5-enoate | HMDB | 5-Dodecenoic acid | HMDB | FA(12:1(5Z)) | HMDB | Lauroleinate | HMDB |
|
---|
Chemical Formula | C12H22O2 |
---|
Average Mass | 198.3019 Da |
---|
Monoisotopic Mass | 198.16198 Da |
---|
IUPAC Name | (5Z)-dodec-5-enoic acid |
---|
Traditional Name | cis-5-dodecenoic acid |
---|
CAS Registry Number | 2430-94-6 |
---|
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 Key | IJBFSOLHRKELLR-FPLPWBNLSA-N |
---|
Experimental Spectra |
---|
|
| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
---|
|
| Not Available | Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Fatty Acyls |
---|
Sub Class | Fatty acids and conjugates |
---|
Direct Parent | Medium-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 Framework | Aliphatic acyclic compounds |
---|
External Descriptors | |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 9.12 mg/L @ 25 °C (est) | The Good Scents Company Information System | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
|
---|