Hydroxychavicol

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	1126-61-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL111134;
ChemSpider	63940;
ECHA InfoCard	100.208.658
EC Number	683-143-7;
PubChem CID	70775;
UNII	FG58C4J9BR ;
CompTox Dashboard (EPA)	DTXSID20150112 ;
	InChI InChI=1S/C9H10O2/c1-2-3-7-4-5-8(10)9(11)6-7/h2,4-6,10-11H,1,3H2 Key: FHEHIXJLCWUPCZ-UHFFFAOYSA-N;
	SMILES C=CCC1=CC(=C(C=C1)O)O;
Properties
Chemical formula	C9H10O2
Molar mass	150.177 g·mol−1
Hazards
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). Infobox references

Hydroxychavicol is a phenylpropanoid compound present in leaves of Piper betle.^[1] It is a more potent inhibitor of xanthine oxidase (IC₅₀=16.7 μM) than allopurinol.^[2]^[3]

Research

It might be a useful new compound in treating cutaneous fungal infections.^[4] 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.^[5]^[6]^[7]^[8]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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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[pmid30169967-1] 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.

[pmid19387769-2] 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.

[pmid29695658-3] 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.

[pmid27897199-4] 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.

[pmid32155466-5] 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.

[AliKhan2010-6] 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.

[Himratul-AznitaNor-Zulaila2016-7] 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.

[MailHimratul-Aznita2017-8] 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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[5]

[6]

[7]

[8]

Research

See also

References