From Wikipedia, the free encyclopedia
Bilobol
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Names
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Preferred IUPAC name
5-[(8Z)-Pentadec-8-enyl]benzene-1,3-diol
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Other names
5-[(Z)-Pentadec-8-en-1-yl]resorcinol 5-Pentadecenylresorcinol
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Identifiers
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ChemSpider
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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
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Oc1cc(cc(O)c1)CCCCCCC\C=C/CCCCCC CCCCCCC=CCCCCCCCC1=CC(=CC(=C1)O)O
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Properties
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C21H34O2
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Molar mass
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318.501 g·mol−1
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Bilobol is an
alkylresorcinol from
Ginkgo biloba. 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]
References
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^ 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.
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^ 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.
S2CID
25305504.