Record Information |
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Version | 2.0 |
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Created at | 2022-03-17 20:58:19 UTC |
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Updated at | 2022-03-17 20:58:19 UTC |
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NP-MRD ID | NP0048556 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 6-Hydroxyluteolin |
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Description | 6-Hydroxyluteolin, also known as 6-OH-luteolin, belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, 6-hydroxyluteolin is considered to be a flavonoid lipid molecule. 6-Hydroxyluteolin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 6-Hydroxyluteolin is found, on average, in the highest concentration within mexican oregano. 6-Hydroxyluteolin has also been detected, but not quantified in, a few different foods, such as common thymes, green vegetables, and lemon verbena. This could make 6-hydroxyluteolin a potential biomarker for the consumption of these foods. 6-Hydroxyluteolin is found in Aloysia citrodora, Artemisia tridentata, Buddleja globosa, Catalpa bignonioides, Centaurea bracteata, Centaurea bracteata Scop., Crocus sativus , Daphne laureola, Dendroviguiera quinqueradiata, Globularia bisnagarica, Globularia vulgaris, Lepidagathis cristata, Lippia citriodora , Phyla nodiflora, Lippia origanoides, Persicaria hydropiper, Polygonum hydropiper L. , Tabebuia caraiba, Tecoma australis, Thymus moroderi , Valerianella eriocarpa , Veronica hederifolia and Veronica triloba. 6-Hydroxyluteolin was first documented in 1999 (PMID: 10048707). A pentahydroxyflavone that is luteolin with an additional hydroxy group at position 6 (PMID: 12693635) (PMID: 19666078) (PMID: 21236437). |
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Structure | OC1=CC2=C(C(O)=C1O)C(=O)C=C(O2)C1=CC(O)=C(O)C=C1 InChI=1S/C15H10O7/c16-7-2-1-6(3-8(7)17)11-4-9(18)13-12(22-11)5-10(19)14(20)15(13)21/h1-5,16-17,19-21H |
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Synonyms | Value | Source |
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2-(3,4-Dihydroxyphenyl)-5,6,7-trihydroxy-4H-1-benzopyran-4-one | ChEBI | 3',4',5,6,7-Pentahydroxyflavone | ChEBI | 5,6,7,3',4'-Pentahydroxyflavone | ChEBI | 2-(3,4-Dihydroxyphenyl)-5,6,7-trihydroxy-4H-chromen-4-one | HMDB | 6-OH-Luteolin | HMDB |
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Chemical Formula | C15H10O7 |
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Average Mass | 302.2357 Da |
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Monoisotopic Mass | 302.04265 Da |
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IUPAC Name | 2-(3,4-dihydroxyphenyl)-5,6,7-trihydroxy-4H-chromen-4-one |
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Traditional Name | 6-hydroxyluteolin |
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CAS Registry Number | 18003-33-3 |
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SMILES | OC1=CC2=C(C(O)=C1O)C(=O)C=C(O2)C1=CC(O)=C(O)C=C1 |
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InChI Identifier | InChI=1S/C15H10O7/c16-7-2-1-6(3-8(7)17)11-4-9(18)13-12(22-11)5-10(19)14(20)15(13)21/h1-5,16-17,19-21H |
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InChI Key | VYAKIUWQLHRZGK-UHFFFAOYSA-N |
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Experimental Spectra |
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| Not Available |
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Predicted Spectra |
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| Not Available |
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Chemical Shift Submissions |
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| Not Available |
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Species |
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Species of Origin | | Show more...
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Flavonoids |
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Sub Class | Flavones |
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Direct Parent | Flavones |
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Alternative Parents | |
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Substituents | - 3'-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- Flavone
- 6-hydroxyflavonoid
- 7-hydroxyflavonoid
- Hydroxyflavonoid
- Chromone
- Benzopyran
- 1-benzopyran
- Catechol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Pyranone
- Benzenoid
- Monocyclic benzene moiety
- Pyran
- Heteroaromatic compound
- Vinylogous acid
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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