Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:12:35 UTC |
---|
Update date | 2019-11-26 03:13:39 UTC |
---|
Primary ID | FDB016702 |
---|
Secondary Accession Numbers | Not Available |
---|
Chemical Information |
---|
FooDB Name | Cirsilineol |
---|
Description | Cirsilineol, also known as 4',5-dihydroxy-3',6,7-trimethoxy-flavone or anisomelin, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, cirsilineol is considered to be a flavonoid lipid molecule. Cirsilineol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cirsilineol can be found in a number of food items such as common thyme, tarragon, common sage, and hyssop, which makes cirsilineol a potential biomarker for the consumption of these food products. Cirsilineol is a bioactive flavone isolated from Artemisia and from Teucrium gnaphalodes . |
---|
CAS Number | 41365-32-6 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
Anisomelin | MetaCyc | 5,4'-Dihydroxy-6,7,3'-trimethoxyflavone | MetaCyc | Eupatrin | MetaCyc | Fastigenin | MetaCyc | 5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one | MetaCyc | 4',5-Dihydroxy-3',6,7-trimethoxyflavone | MeSH | 4',5-Dihydroxy-3',6,7-trimethoxy-flavone | MeSH | Cirsilineol | db_source | Cirsilineol (5,4'-dihydroxy-6,7,3'-trimethoxyflavone) | biospider |
|
---|
Predicted Properties | |
---|
Chemical Formula | C18H16O7 |
---|
IUPAC name | 5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7-dimethoxy-4H-chromen-4-one |
---|
InChI Identifier | InChI=1S/C18H16O7/c1-22-13-6-9(4-5-10(13)19)12-7-11(20)16-14(25-12)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3 |
---|
InChI Key | VKOSQMWSWLZQPA-UHFFFAOYSA-N |
---|
Isomeric SMILES | COC1=CC2=C(C(=O)C=C(O2)C2=CC(OC)=C(O)C=C2)C(O)=C1OC |
---|
Average Molecular Weight | 344.3154 |
---|
Monoisotopic Molecular Weight | 344.089602866 |
---|
Classification |
---|
Description | Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. |
---|
Kingdom | Organic compounds |
---|
Super Class | Phenylpropanoids and polyketides |
---|
Class | Flavonoids |
---|
Sub Class | O-methylated flavonoids |
---|
Direct Parent | 7-O-methylated flavonoids |
---|
Alternative Parents | |
---|
Substituents | - 3p-methoxyflavonoid-skeleton
- 6-methoxyflavonoid-skeleton
- 7-methoxyflavonoid-skeleton
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- Flavone
- Hydroxyflavonoid
- Chromone
- Benzopyran
- Methoxyphenol
- 1-benzopyran
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- 1-hydroxy-4-unsubstituted benzenoid
- Alkyl aryl ether
- Benzenoid
- Pyran
- Monocyclic benzene moiety
- Vinylogous acid
- Heteroaromatic compound
- Organoheterocyclic compound
- Oxacycle
- Ether
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic heteropolycyclic compound
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Ontology | No ontology term |
---|
Physico-Chemical Properties - Experimental |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Not Available | |
---|
Physical Description | Not Available | |
---|
Mass Composition | C 62.79%; H 4.68%; O 32.53% | DFC |
---|
Melting Point | Mp 208-210° (203°) | DFC |
---|
Boiling Point | Not Available | |
---|
Experimental Water Solubility | Not Available | |
---|
Experimental logP | Not Available | |
---|
Experimental pKa | Not Available | |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | Not Available | |
---|
Spectroscopic UV Data | Not Available | |
---|
Density | Not Available | |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Not Available |
---|
MS/MS | Type | Description | Splash Key | View |
---|
Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0009000000-dc1a431c47b12ff35d6f | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-0009000000-83f5a1606a8c1db30b43 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0002-0693000000-2135cd96963ff8bae9a3 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0009000000-d849bd5042cabc197d52 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0029000000-91a37534990e9343e565 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ar4-0291000000-9206d9f37362017c1a95 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0009000000-5dc8eb0c39637af07086 | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-0009000000-5dc6fda56294b4fda1a7 | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-0109000000-90d350448efbe259f79b | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0009000000-72fbd0eb75bc9ea05c55 | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0f96-0009000000-176ea7d83528de995c1f | 2021-10-21 | View Spectrum |
|
---|
NMR | Not Available |
---|
External Links |
---|
ChemSpider ID | Not Available |
---|
ChEMBL ID | Not Available |
---|
KEGG Compound ID | C10032 |
---|
Pubchem Compound ID | 162464 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | 276 |
---|
DrugBank ID | Not Available |
---|
HMDB ID | Not Available |
---|
CRC / DFC (Dictionary of Food Compounds) ID | KDD85-Q:KSN20-S |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | CIRSILINEOL |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | C00013595 |
---|
HET ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Not Available |
---|
Phenol-Explorer Metabolite ID | Not Available |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | |
---|
Enzymes | Not Available |
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Not Available |
---|
Files |
---|
MSDS | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
Content Reference | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070. — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
|
---|