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Record Information
Version2.0
Created at2022-03-17 20:58:19 UTC
Updated at2022-03-17 20:58:19 UTC
NP-MRD IDNP0048556
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-Hydroxyluteolin
Description6-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).
Structure
Thumb
Synonyms
ValueSource
2-(3,4-Dihydroxyphenyl)-5,6,7-trihydroxy-4H-1-benzopyran-4-oneChEBI
3',4',5,6,7-PentahydroxyflavoneChEBI
5,6,7,3',4'-PentahydroxyflavoneChEBI
2-(3,4-Dihydroxyphenyl)-5,6,7-trihydroxy-4H-chromen-4-oneHMDB
6-OH-LuteolinHMDB
Chemical FormulaC15H10O7
Average Mass302.2357 Da
Monoisotopic Mass302.04265 Da
IUPAC Name2-(3,4-dihydroxyphenyl)-5,6,7-trihydroxy-4H-chromen-4-one
Traditional Name6-hydroxyluteolin
CAS Registry Number18003-33-3
SMILES
OC1=CC2=C(C(O)=C1O)C(=O)C=C(O2)C1=CC(O)=C(O)C=C1
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
InChI KeyVYAKIUWQLHRZGK-UHFFFAOYSA-N
Experimental Spectra
Not Available
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 flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.36ALOGPS
logP2.1ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.8ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.45 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.88 m³·mol⁻¹ChemAxon
Polarizability28.67 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036632
DrugBank IDNot Available
Phenol Explorer Compound ID278
FoodDB IDFDB015551
KNApSAcK IDC00003884
Chemspider ID4444961
KEGG Compound IDC10072
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281642
PDB IDNot Available
ChEBI ID2197
Good Scents IDNot Available
References
General References
  1. Yokozawa T, Dong E, Kawai Y, Gemba M, Shimizu M: Protective effects of some flavonoids on the renal cellular membrane. Exp Toxicol Pathol. 1999 Jan;51(1):9-14. doi: 10.1016/S0940-2993(99)80050-5. [PubMed:10048707 ]
  2. Greenham J, Harborne JB, Williams CA: Identification of lipophilic flavones and flavonols by comparative HPLC, TLC and UV spectral analysis. Phytochem Anal. 2003 Mar-Apr;14(2):100-18. doi: 10.1002/pca.693. [PubMed:12693635 ]
  3. Androutsopoulos VP, Ruparelia K, Arroo RR, Tsatsakis AM, Spandidos DA: CYP1-mediated antiproliferative activity of dietary flavonoids in MDA-MB-468 breast cancer cells. Toxicology. 2009 Oct 29;264(3):162-70. doi: 10.1016/j.tox.2009.07.023. Epub 2009 Aug 8. [PubMed:19666078 ]
  4. de Beer D, Joubert E, Malherbe CJ, Jacobus Brand D: Use of countercurrent chromatography during isolation of 6-hydroxyluteolin-7-O-beta-glucoside, a major antioxidant of Athrixia phylicoides. J Chromatogr A. 2011 Sep 9;1218(36):6179-86. doi: 10.1016/j.chroma.2010.12.096. Epub 2010 Dec 29. [PubMed:21236437 ]