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Quinone methide information


Quinone methide
Identifiers
CAS Number
  • p-: 502-87-4
3D model (JSmol)
  • o-: Interactive image
  • p-: Interactive image
Beilstein Reference
1922177
ChEBI
  • o-: CHEBI:52409
  • p-: CHEBI:52406
PubChem CID
  • o-: 13265823
  • p-: 136328
UNII
  • V9FUL88GTN checkY
InChI
  • o-: InChI=1S/C7H6O/c1-6-4-2-3-5-7(6)8/h2-5H,1H2
    Key: NSDWWGAIPUNJAX-UHFFFAOYSA-N
  • p-: InChI=1S/C7H6O/c1-6-2-4-7(8)5-3-6/h2-5H,1H2
    Key: OJPNKYLDSDFUPG-UHFFFAOYSA-N
SMILES
  • o-: C=C1C=CC=CC1=O
  • p-: C=C1C=CC(=O)C=C1
Properties
Chemical formula
C7H6O
Molar mass 106.124 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

A quinone methide is a type of conjugated organic compound that contain a cyclohexadiene with a carbonyl and an exocyclic methylidene or extended alkene unit. It is analogous to a quinone, but having one of the double bonded oxygens replaced with a carbon. The carbonyl and methylidene are usually oriented either ortho or para to each other. There are some examples of transient synthetic meta quinone methides.

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Quinone methide

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A quinone methide is a type of conjugated organic compound that contain a cyclohexadiene with a carbonyl and an exocyclic methylidene or extended alkene...

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Quinone

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after it ("anthra-1,4-quinone"). Quinone methide – where one O is replaced by C Xylylene – where both O's are replaced by C's Quinone imine – where one O...

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Celastrol

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threewingnut). Celastrol is a pentacyclic nortriterpen quinone and belongs to the family of quinone methides. In mice, celastrol is an NR4A1 agonist that alleviates...

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Bobgunnia madagascariensis

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saponin tetraglycoside. The root bark of B. madagascariensis contains quinone methide diterpenes. The seed pod contains two acidic saponins, swartziasaponin...

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Polymer stabilizer

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nonradical products The end products of these reactions are typically quinone methides, which may also impart unwanted colour. Modern phenolic antioxidants...

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Polymerisation inhibitor

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Jan; Nešpůrek, Stanislav; Zweifel, Hans (October 1996). "The role of quinone methides in thermostabilization of hydrocarbon polymers —II. Properties and...

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Troglitazone

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chromane rings of troglitazone. Moreover, the formation of quinone and o-quinone methide reactive metabolites were proposed to be formed by metabolic...

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Xylylene

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C6H4(CH2)2. These compounds are related to the corresponding quinones and quinone methides by replacement of the oxygen atoms by CH2 groups. ortho- and para-xylylene...

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Polyphenol oxidase

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ISSN 1439-4227. PMC 8049008. PMID 33108057. Sugumaran M, Lipke H (May 1983). "Quinone methide formation from 4-alkylcatechols: a novel reaction catalyzed by cuticular...

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Succinate dehydrogenase

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system, the mechanism of FAD attachment has been shown to involve a quinone:methide intermediate. In mitochondrial, but not bacterial, assembly, SDHA interacts...

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CYP3A4

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to 4-hydroxy-tamoxifen and then dehydrated to 4-hydroxy-tamoxifen quinone methide. Two mechanisms have been proposed as the primary pathway of hydroxylation...

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Taxodone

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has also been patented. Taxodone was the first isolated example of a quinone methide with a labile hydrogen adjacent to this reactive chromophore. Kupchan...

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Michael addition reaction

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Samanta, Sampak (17 July 2020). "1,6-Aza-Michael addition of para-quinone methides with N-heterocycles catalyzed by Zn(OTf)2: A regioselective approach...

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Chavicol

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then leaves thus forming a cation, this cation can be regarded as a quinone methide which then is reduced by NADPH to form either anol or chavicol. Estragole...

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Variegatic acid

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is exposed to air, the chemical is enzymatically oxidized to blue quinone methide anions, specifically chinonmethid anions. It is derived from xerocomic...

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Totarol

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hypothesized to be due to the natural product's ability to form an o-quinone methide in vivo. Totarol also prevents cells from undergoing oxidative stress...

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Kendomycin

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Kendomycin is an anticancer macrolide first isolated from Streptomyces violaceoruber. It has potent activity as an endothelin receptor antagonist and anti-osteoporosis...

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Russulaceae

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Steffan B, Steglich W, Marumoto R (1995). "A novel type of triterpenoid quinone methide pigment from the toadstool Russula flavida (Agaricales)". Tetrahedron...

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Suillus variegatus

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is exposed to air, the chemical is enzymatically oxidized to blue quinone methide anions. Suillus variegatus appears frequently with, and is mycorrhizal...

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Russula flavida

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Steffan B, Steglich W, Marumoto R (1995). "A novel type of triterpenoid quinone methide pigment from the toadstool Russula flavida (Agaricales)". Tetrahedron...

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Protecting group

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L. Dax: "An efficient desilylation method for the generation of o-quinone methides: application to the synthesis of (+)- and (−)-hexahydrocannabinol"...

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John Ralph

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Berkeley University of Wisconsin-Madison Thesis Reactions of lignin model quinone methides and NMR studies of lignins (1982) Doctoral advisor Raymond A. Young...

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Carpanone

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olefin tails—shown crossing in the image—to give a dimeric trans-ortho-quinone methide-type of lignan intermediate. A particular conformation of this dimer...

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Anthocyanone A

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C; Teissedre, PL; Monti, JP; Glories, Y (2007). "Anthocyanone A: A quinone methide derivative resulting from malvidin 3-O-glucoside degradation". Journal...

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Chamaecydin

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Ozaki, Naotake; Iitaka, Yoichi (1983-01-01). "Three new terpenoid quinone methides from the seed of Chamaecyparis obtusa". Tetrahedron Letters. 24 (14):...

Word Count : 939

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