Grevillol

Grevillol
Names
	IUPAC name 5-tridecylbenzene-1,3-diol
	Other names Grevillol; 5-Tridecyl-1,2-benzenediol; 5-Tridecylresorcinol;
Identifiers
CAS Number	5259-01-8;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:5545;
ChEMBL	ChEMBL451044;
ChemSpider	152482;
ECHA InfoCard	100.190.335
EC Number	664-084-6;
KEGG	C10800;
PubChem CID	174862;
CompTox Dashboard (EPA)	DTXSID60200564 ;
	InChI InChI=1S/C19H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-14-18(20)16-19(21)15-17/h14-16,20-21H,2-13H2,1H3 Key: UXOGOSLLGMYCNL-UHFFFAOYSA-N;
	SMILES CCCCCCCCCCCCCC1=CC(=CC(=C1)O)O;
Properties
Chemical formula	C19H32O2
Molar mass	292.463 g·mol−1
Appearance	White solid
Melting point	81-82 °C
Solubility in water	2.14×10−2 mg/L
Vapor pressure	1.73×10−6 Pa
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H317, H318
Precautionary statements	P261, P264+P265, P272, P280, P302+P352, P305+P354+P338, P317, P321, P333+P317, P362+P364, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Grevillol is an alkylresorcinol with a tridecyl side chain. It is a white solid and a natural product, occurring in several species. It is also an allergic contact sensitizer^[4] and exhibits cytotoxicity.^[5]

Occurrence

Grevillol is found in several Grevillea species native to Australia,^[6] notably Grevillea robusta.^[4] It also occurs in Australian brown algae species, including Cystophora torulosa and Caulocystis cephalornithos.^[6]

Reactions

Grevillol can be used as a precursor in the synthesis of rapanone, a 2,5-dihydroxy-1,4-benzoquinone derivative.^[7]

External links

Natural Products Online

References

1 2 Alonso, Emma; Ramón, Diego J.; Yus, Miguel (1997-01-01). "Simple Synthesis of 5-Substituted Resorcinols: A Revisited Family of Interesting Bioactive Molecules". The Journal of Organic Chemistry. 62 (2): 417–421. doi:10.1021/jo9610624. ISSN 0022-3263. PMID 11671418.
1 2 Mollo, E.; Garson, M. J.; Polese, G.; Amodeo, P.; Ghiselin, M. T. (2017-05-10). "Taste and smell in aquatic and terrestrial environments". Natural Product Reports. 34 (5): 496–513. doi:10.1039/C7NP00008A. ISSN 1460-4752. PMID 28443894.
↑ PubChem. "Grevillol". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-01-22.
1 2 Rozas-Muñoz, E.; Lepoittevin, J. P.; Pujol, R. M.; Giménez-Arnau, A. (2012-07-01). "Allergic Contact Dermatitis to Plants: Understanding the Chemistry will Help our Diagnostic Approach". Actas Dermo-Sifiliográficas. 103 (6): 468. doi:10.1016/j.ad.2011.07.017. ISSN 0001-7310. PMID 22217935.
↑ Arisawa, Munehisa; Ohmura, Kazunob; Kobayashi, Akio; Morita, Naokata (1989). "A Cytotoxic Constituent of Lysimachia japonica THUNB. (Primulaceae) and the Structure-Activity Relationships of Related Compounds". Chemical & Pharmaceutical Bulletin. 37 (9): 2431–2434. doi:10.1248/cpb.37.2431. PMID 2605686.
1 2 Capon, Robert J. (2001). "Marine Bioprospecting − Trawling for Treasure and Pleasure". European Journal of Organic Chemistry. 2001 (4): 642. doi:10.1002/1099-0690(200102)2001:4<633::AID-EJOC633>3.0.CO;2-Q. ISSN 1099-0690.
↑ Croft, Ja; Ritchie, E; Taylor, Wc (1976-09-01). "Chemical studies of the Proteaceae. VIII. The conversion of grevillol into rapanone and experiments on the synthesis of ardisiaquinone A". Australian Journal of Chemistry. 29 (9): 1979–1987. doi:10.1071/CH9761979. ISSN 0004-9425.

[alonso-1] 1 2 Alonso, Emma; Ramón, Diego J.; Yus, Miguel (1997-01-01). "Simple Synthesis of 5-Substituted Resorcinols: A Revisited Family of Interesting Bioactive Molecules". The Journal of Organic Chemistry. 62 (2): 417–421. doi:10.1021/jo9610624. ISSN 0022-3263. PMID 11671418.

[mollo-2] 1 2 Mollo, E.; Garson, M. J.; Polese, G.; Amodeo, P.; Ghiselin, M. T. (2017-05-10). "Taste and smell in aquatic and terrestrial environments". Natural Product Reports. 34 (5): 496–513. doi:10.1039/C7NP00008A. ISSN 1460-4752. PMID 28443894.

[3] PubChem. "Grevillol". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-01-22.

[rozas-4] 1 2 Rozas-Muñoz, E.; Lepoittevin, J. P.; Pujol, R. M.; Giménez-Arnau, A. (2012-07-01). "Allergic Contact Dermatitis to Plants: Understanding the Chemistry will Help our Diagnostic Approach". Actas Dermo-Sifiliográficas. 103 (6): 468. doi:10.1016/j.ad.2011.07.017. ISSN 0001-7310. PMID 22217935.

[5] Arisawa, Munehisa; Ohmura, Kazunob; Kobayashi, Akio; Morita, Naokata (1989). "A Cytotoxic Constituent of Lysimachia japonica THUNB. (Primulaceae) and the Structure-Activity Relationships of Related Compounds". Chemical & Pharmaceutical Bulletin. 37 (9): 2431–2434. doi:10.1248/cpb.37.2431. PMID 2605686.

[capon-6] 1 2 Capon, Robert J. (2001). "Marine Bioprospecting − Trawling for Treasure and Pleasure". European Journal of Organic Chemistry. 2001 (4): 642. doi:10.1002/1099-0690(200102)2001:4<633::AID-EJOC633>3.0.CO;2-Q. ISSN 1099-0690.

[7] Croft, Ja; Ritchie, E; Taylor, Wc (1976-09-01). "Chemical studies of the Proteaceae. VIII. The conversion of grevillol into rapanone and experiments on the synthesis of ardisiaquinone A". Australian Journal of Chemistry. 29 (9): 1979–1987. doi:10.1071/CH9761979. ISSN 0004-9425.

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Occurrence

Reactions

External links

References