Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2012-09-11 23:09:34 UTC |
---|
Update Date | 2022-03-07 02:55:33 UTC |
---|
HMDB ID | HMDB0037906 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Hernandulcin |
---|
Description | Hernandulcin is a constituent of Lippia dulcis leaves and flowers. Natural sweetener more than 1000 times sweeter than sucrose Hernandulcin is a sesquiterpene with the molecular formula C15H24O2. By slightly modifying the compound, researchers have identified the two chemical groups which caused the sweet taste - the carbonyl group, and the hydroxyl group. The structure of hernandulcin is very simple, and after a panel of volunteers tasted hernandulcin, it was determined that it was 1,000 times sweeter than sugar. Hernandulcin also has a bitter aftertaste, and does not cause tooth decay, which would make it a good candidate for a mouthwash. Hernandulcin is an intensely sweet chemical compound gained from the chiefly Mexican and South American plant Lippia dulcis. |
---|
Structure | CC(C)=CCCC(C)(O)C1CCC(C)=CC1=O InChI=1S/C15H24O2/c1-11(2)6-5-9-15(4,17)13-8-7-12(3)10-14(13)16/h6,10,13,17H,5,7-9H2,1-4H3 |
---|
Synonyms | Not Available |
---|
Chemical Formula | C15H24O2 |
---|
Average Molecular Weight | 236.3499 |
---|
Monoisotopic Molecular Weight | 236.177630012 |
---|
IUPAC Name | 6-(2-hydroxy-6-methylhept-5-en-2-yl)-3-methylcyclohex-2-en-1-one |
---|
Traditional Name | 6-(2-hydroxy-6-methylhept-5-en-2-yl)-3-methylcyclohex-2-en-1-one |
---|
CAS Registry Number | 95602-94-1 |
---|
SMILES | CC(C)=CCCC(C)(O)C1CCC(C)=CC1=O |
---|
InChI Identifier | InChI=1S/C15H24O2/c1-11(2)6-5-9-15(4,17)13-8-7-12(3)10-14(13)16/h6,10,13,17H,5,7-9H2,1-4H3 |
---|
InChI Key | HYQNKKAJVPMBDR-UHFFFAOYSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Prenol lipids |
---|
Sub Class | Sesquiterpenoids |
---|
Direct Parent | Sesquiterpenoids |
---|
Alternative Parents | |
---|
Substituents | - Bisabolane sesquiterpenoid
- Sesquiterpenoid
- Cyclohexenone
- Tertiary alcohol
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic homomonocyclic compound
|
---|
Molecular Framework | Aliphatic homomonocyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | |
---|
Role | |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Molecular Properties | |
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | | Show more...
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
Hernandulcin,1TMS,isomer #1 | CC(C)=CCCC(C)(O[Si](C)(C)C)C1CCC(C)=CC1=O | 1972.1 | Semi standard non polar | 33892256 | Hernandulcin,1TMS,isomer #2 | CC(C)=CCCC(C)(O)C1=C(O[Si](C)(C)C)C=C(C)CC1 | 1935.4 | Semi standard non polar | 33892256 | Hernandulcin,2TMS,isomer #1 | CC(C)=CCCC(C)(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C(C)CC1 | 1994.1 | Semi standard non polar | 33892256 | Hernandulcin,2TMS,isomer #1 | CC(C)=CCCC(C)(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C=C(C)CC1 | 1972.7 | Standard non polar | 33892256 | Hernandulcin,1TBDMS,isomer #1 | CC(C)=CCCC(C)(O[Si](C)(C)C(C)(C)C)C1CCC(C)=CC1=O | 2208.0 | Semi standard non polar | 33892256 | Hernandulcin,1TBDMS,isomer #2 | CC(C)=CCCC(C)(O)C1=C(O[Si](C)(C)C(C)(C)C)C=C(C)CC1 | 2173.2 | Semi standard non polar | 33892256 | Hernandulcin,2TBDMS,isomer #1 | CC(C)=CCCC(C)(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C(C)CC1 | 2459.6 | Semi standard non polar | 33892256 | Hernandulcin,2TBDMS,isomer #1 | CC(C)=CCCC(C)(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C=C(C)CC1 | 2370.0 | Standard non polar | 33892256 |
| Show more...
---|
Spectra |
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - Hernandulcin GC-MS (Non-derivatized) - 70eV, Positive | splash10-016r-9210000000-8d1cf7e503b734e8ace1 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hernandulcin GC-MS (1 TMS) - 70eV, Positive | splash10-006x-9230000000-438e014564b699a21090 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hernandulcin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hernandulcin 10V, Positive-QTOF | splash10-014r-0390000000-6ed83e70722d3fd3bf0e | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hernandulcin 20V, Positive-QTOF | splash10-014i-4940000000-02e21219bcfae41388f7 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hernandulcin 40V, Positive-QTOF | splash10-0gb9-9500000000-093e36227243e20a8baf | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hernandulcin 10V, Negative-QTOF | splash10-000i-0190000000-e44deea8a6a69cec8d49 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hernandulcin 20V, Negative-QTOF | splash10-0a4r-1950000000-6ef86ce6dee42cb3a431 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hernandulcin 40V, Negative-QTOF | splash10-0a4i-7900000000-6727793c76ad9079a7bd | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hernandulcin 10V, Positive-QTOF | splash10-03yr-1920000000-0f2144bb085689d94221 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hernandulcin 20V, Positive-QTOF | splash10-066r-9810000000-2bf98549b059d7168644 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hernandulcin 40V, Positive-QTOF | splash10-05mo-9000000000-c127019f7213afec2fdb | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hernandulcin 10V, Negative-QTOF | splash10-000i-0090000000-c0031dc201eac6b6350a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hernandulcin 20V, Negative-QTOF | splash10-052r-0890000000-7ee6b1e64ee53ab1c532 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hernandulcin 40V, Negative-QTOF | splash10-0a4l-7900000000-ebd8c80bbe4a05800d1b | 2021-09-24 | Wishart Lab | View Spectrum |
| Show more...
---|
Biological Properties |
---|
Cellular Locations | |
---|
Biospecimen Locations | Not Available |
---|
Tissue Locations | Not Available |
---|
Pathways | |
---|
Normal Concentrations |
---|
| Not Available |
---|
Abnormal Concentrations |
---|
| Not Available |
---|
Associated Disorders and Diseases |
---|
Disease References | None |
---|
Associated OMIM IDs | None |
---|
External Links |
---|
DrugBank ID | Not Available |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | FDB017062 |
---|
KNApSAcK ID | C00003144 |
---|
Chemspider ID | 2744198 |
---|
KEGG Compound ID | Not Available |
---|
BioCyc ID | Not Available |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Hernandulcin |
---|
METLIN ID | Not Available |
---|
PubChem Compound | 3504251 |
---|
PDB ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
MarkerDB ID | Not Available |
---|
Good Scents ID | rw1511361 |
---|
References |
---|
Synthesis Reference | Not Available |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
General References | - Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
- Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
- Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
|
---|