Bilobol

Bilobol
Names
	IUPAC name 5-[(Z)-Pentadec-8-enyl]benzene-1,3-diol
	Other names 5-[(Z)-Pentadec-8-enylo]resorcinol; 5-Pentadecenylresorcinol
Identifiers
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	4445147;
PubChem CID	5281852;
CompTox Dashboard (EPA)	DTXSID90872874 ;
	InChI InChI=1S/C21H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-20(22)18-21(23)17-19/h7-8,16-18,22-23H,2-6,9-15H2,1H3/b8-7- Key: TUGAUFMQYWZJAB-FPLPWBNLSA-N; InChI=1/C21H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-16-20(22)18-21(23)17-19/h7-8,16-18,22-23H,2-6,9-15H2,1H3/b8-7- Key: TUGAUFMQYWZJAB-FPLPWBNLBC;
	SMILES Oc1cc(cc(O)c1)CCCCCCC\C=C/CCCCCC; CCCCCCC=CCCCCCCCC1=CC(=CC(=C1)O)O;
Properties
Chemical formula	C21H34O2
Molar mass	318.501 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

Bilobol is an alkylresorcinol, a type of phenolic lipids composed of long aliphatic chains and phenolic rings. Chemically, it is similar in structure to urushiol, the irritant found in poison ivy; it is a strong skin irritant itself.[1]

Natural occurrences

Bilobol can be found in Ginkgo biloba fruits.[2]

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gollark: You also agree that unless you disable backdoors in potatOS before installation, data available via these may be used at any time for the purposes of remote debugging, analysis of what potatOS users have installed, or random messing around. You also agree that your soul is forfeit to me.

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References

Matsumoto, Kazuyuk i; Fujimoto, Masao; Ito, Kazuo; Tanaka, Hitoshi; Hirono, Iwao (1990). "Comparison of the effects of bilobol and 12-O-tetradecanoylphorbol-13-acetate on skin, and test of tumor promoting potential of bilobol in CD-1 mice". The Journal of Toxicological Sciences. 15 (1): 39–46. doi:10.2131/jts.15.39. PMID 2110595.
Tanaka, A; Arai, Y; Kim, SN; Ham, J; Usuki, T (2011). "Synthesis and biological evaluation of bilobol and adipostatin A". Journal of Asian natural products research. 13 (4): 290–6. doi:10.1080/10286020.2011.554828. PMID 21462031.

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[1] Matsumoto, Kazuyuk i; Fujimoto, Masao; Ito, Kazuo; Tanaka, Hitoshi; Hirono, Iwao (1990). "Comparison of the effects of bilobol and 12-O-tetradecanoylphorbol-13-acetate on skin, and test of tumor promoting potential of bilobol in CD-1 mice". The Journal of Toxicological Sciences. 15 (1): 39–46. doi:10.2131/jts.15.39. PMID 2110595.

[2] Tanaka, A; Arai, Y; Kim, SN; Ham, J; Usuki, T (2011). "Synthesis and biological evaluation of bilobol and adipostatin A". Journal of Asian natural products research. 13 (4): 290–6. doi:10.1080/10286020.2011.554828. PMID 21462031.