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Hydroxychavicol

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(Redirected from Desmethylisoeugenol)
Hydroxychavicol
Names
Preferred IUPAC name 4-(Prop-2-en-1-yl)benzene-1,2-diol
Other names
  • 4-Allylbenzene-1,2-diol
  • Allylpyrocatechol
  • 4-Allylpyrocatechol
  • Desmethylisoeugenol
  • 3,4-dihydroxy-allylbenzene
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.208.658 Edit this at Wikidata
EC Number
  • 683-143-7
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H10O2/c1-2-3-7-4-5-8(10)9(11)6-7/h2,4-6,10-11H,1,3H2Key: FHEHIXJLCWUPCZ-UHFFFAOYSA-N
SMILES
  • C=CCC1=CC(=C(C=C1)O)O
Properties
Chemical formula C9H10O2
Molar mass 150.177 g·mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H312, H315, H319
Precautionary statements P264, P270, P280, P301+P312, P302+P352, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Hydroxychavicol is a phenylpropanoid compound present in leaves of Piper betle. It is a more potent inhibitor of xanthine oxidase (IC50=16.7 μM) than allopurinol.

Research

It might be a useful new compound in treating cutaneous fungal infections. It is a promising agent in prevention and treatment of dental disorders as it had bactericidal and fungicidal effect on Streptococcus intermedius, Streptococcus mutans, and Candida albicans and inhibited biofilm formation.

See also

References

  1. Atiya A, Sinha BN, Lal UR (March 2020). "The new ether derivative of phenylpropanoid and bioactivity was investigated from the leaves of Piper betle L". Natural Product Research. 34 (5): 638–645. doi:10.1080/14786419.2018.1495634. PMID 30169967. S2CID 52139286.
  2. Murata K, Nakao K, Hirata N, Namba K, Nomi T, Kitamura Y, Moriyama K, Shintani T, Iinuma M, Matsuda H (July 2009). "Hydroxychavicol: a potent xanthine oxidase inhibitor obtained from the leaves of betel, Piper betle". Journal of Natural Medicines. 63 (3): 355–9. doi:10.1007/s11418-009-0331-y. PMID 19387769. S2CID 19647900.
  3. Nishiwaki K, Ohigashi K, Deguchi T, Murata K, Nakamura S, Matsuda H, Nakanishi I (July 2018). "Structure-Activity Relationships and Docking Studies of Hydroxychavicol and Its Analogs as Xanthine Oxidase Inhibitors". Chemical & Pharmaceutical Bulletin. 66 (7): 741–747. doi:10.1248/cpb.c18-00197. PMID 29695658.
  4. Ali I, Satti NK, Dutt P, Prasad R, Khan IA (November 2016). "Hydroxychavicol: A phytochemical targeting cutaneous fungal infections". Scientific Reports. 6: 37867. Bibcode:2016NatSR...637867A. doi:10.1038/srep37867. PMC 5126685. PMID 27897199.
  5. Phumat P, Khongkhunthian S, Wanachantararak P, Okonogi S (May 2020). "Comparative inhibitory effects of 4-allylpyrocatechol isolated from Piper betle on Streptococcus intermedius, Streptococcus mutans, and Candida albicans". Archives of Oral Biology. 113: 104690. doi:10.1016/j.archoralbio.2020.104690. PMID 32155466. S2CID 212664434.
  6. Ali, Intzar; Khan, Farrah G; Suri, Krishan A; Gupta, Bishan D; Satti, Naresh K; Dutt, Prabhu; Afrin, Farhat; Qazi, Ghulam N; Khan, Inshad A (2010). "In vitro antifungal activity of hydroxychavicol isolated from Piper betle L". Annals of Clinical Microbiology and Antimicrobials. 9 (1): 7. doi:10.1186/1476-0711-9-7. ISSN 1476-0711. PMC 2841090. PMID 20128889.
  7. Himratul-Aznita, Wan Harun; Nor-Zulaila, Che Omran; Nurul-Fatihah, Khairuddin (2016). "Antifungal activity of dual combination of hydroxychavicol with commercialized agents against oral Candida species". SpringerPlus. 5 (1): 1696. doi:10.1186/s40064-016-3396-6. ISSN 2193-1801. PMC 5047859. PMID 27757368.
  8. Mail, Mohd Hafiz; Himratul-Aznita, Wan Harun; Musa, Md Yusoff (2017). "Anti-hyphal properties of potential bioactive compounds for oral rinse in suppression of Candida growth". Biotechnology & Biotechnological Equipment. 31 (5): 989–999. doi:10.1080/13102818.2017.1348255. ISSN 1310-2818.


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