Record Information |
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Version | 1.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2021-08-19 23:58:53 UTC |
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NP-MRD ID | NP0001181 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Delta-Hexanolactone |
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Description | D-Hexanolactone is the lactone of 5-hydroxy-Hexanoic acid. Lactones are internal esters that exist in equilibrium between their closed (lactone) and open (hydroxy acid) forms in an aqueous environment. The lactone/hydroxy acid ratio at equilibrium is pH-dependent, with the closed form being favored at lower pH values, and can be greatly influenced by structural features of the lactone such as the ring size, substituents on the ring and the presence of double bonds within the ring. Many drugs and endogenous compounds are lactones or hydroxy acids and an enzyme capable of catalyzing the interchange between the open and closed forms in vivo could have pronounced effects upon their biological activity and/or distribution. D-Hexanolactone is the substrate of paraoxonases (PON) in humans. Human PON1 hydrolyzes over 30 different lactones (cyclic esters) and catalyzes the reverse reaction (lactonization) of a broad range of hydroxy acids. Hydroxy acid lactonization or lactone hydrolysis is catalyzed until equilibrium between the open and closed forms is reached. (PMID 15772423 , 12963475 , 12963475 ). |
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Structure | InChI=1S/C6H10O2/c1-5-3-2-4-6(7)8-5/h5H,2-4H2,1H3 |
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Synonyms | Value | Source |
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Δ-hexanolactone | Generator | Epsilon-Caprolactone | HMDB | (RS)-delta-Hexalactone | HMDB | 5-Hexanolide | HMDB | 5-Hydroxy-hexanoate | HMDB | 5-Hydroxy-hexanoic acid | HMDB | 5-Hydroxy-hexanoic acid lactone | HMDB | 5-Hydroxyhexanoate | HMDB | 5-Hydroxyhexanoic acid | HMDB | 5-Hydroxyhexanoic acid lactone | HMDB | 6-Methyl-D-valerolactone | HMDB | 6-Methylvalerolactone | HMDB | delta-Caprolactone | HMDB | delta-Hexalactone | HMDB | delta-Hexanolide | HMDB | delta-Methyl-delta-valerolactone | HMDB | Hexanolactone | HMDB | Tetrahydro-6-methyl-2H-pyran-2-one | HMDB |
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Chemical Formula | C6H10O2 |
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Average Mass | 114.1424 Da |
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Monoisotopic Mass | 114.06808 Da |
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IUPAC Name | 6-methyloxan-2-one |
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Traditional Name | hexanolactone |
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CAS Registry Number | 823-22-3 |
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SMILES | CC1CCCC(=O)O1 |
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InChI Identifier | InChI=1S/C6H10O2/c1-5-3-2-4-6(7)8-5/h5H,2-4H2,1H3 |
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InChI Key | RZTOWFMDBDPERY-UHFFFAOYSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Lactones |
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Sub Class | Delta valerolactones |
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Direct Parent | Delta valerolactones |
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Alternative Parents | |
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Substituents | - Delta_valerolactone
- Delta valerolactone
- Oxane
- Carboxylic acid ester
- Oxacycle
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Properties | |
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Predicted Properties | |
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General References | - Draganov DI, Teiber JF, Speelman A, Osawa Y, Sunahara R, La Du BN: Human paraoxonases (PON1, PON2, and PON3) are lactonases with overlapping and distinct substrate specificities. J Lipid Res. 2005 Jun;46(6):1239-47. Epub 2005 Mar 16. [PubMed:15772423 ]
- Moser AB, Jones DS, Raymond GV, Moser HW: Plasma and red blood cell fatty acids in peroxisomal disorders. Neurochem Res. 1999 Feb;24(2):187-97. [PubMed:9972864 ]
- Teiber JF, Draganov DI, La Du BN: Lactonase and lactonizing activities of human serum paraoxonase (PON1) and rabbit serum PON3. Biochem Pharmacol. 2003 Sep 15;66(6):887-96. [PubMed:12963475 ]
- Wang X, Zhang Q, Jia Z: A new tricyclic-alpha,beta-unsaturate ketone and a new delta-hexano lactone glycoside from Adenocaulon himalaicum. Nat Prod Res. 2007 Feb;21(2):161-6. doi: 10.1080/14786410601130000. [PubMed:17365704 ]
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