Grevillol

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Grevillol
Grevillol.svg
Names
IUPAC name
5-tridecylbenzene-1,3-diol
Other names
  • Grevillol
  • 5-Tridecyl-1,2-benzenediol
  • 5-Tridecylresorcinol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.190.335 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 664-084-6
KEGG
PubChem CID
  • 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
  • CCCCCCCCCCCCCC1=CC(=CC(=C1)O)O
Properties
C19H32O2
Molar mass 292.463 g·mol−1
AppearanceWhite solid [1]
Melting point 81-82 °C [1]
2.14×10−2 mg/L [2]
Vapor pressure 1.73×10−6 Pa [2]
Hazards
GHS labelling: [3]
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H317, H318
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).

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]

Contents

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]

References

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