pinosylvin
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 361726608
| ImageFile = Pinosylvin.svg
| ImageSize =
| PIN = 5-[(1E)-2-Phenylethen-1-yl]benzene-1,3-diol
| OtherNames = (E)-3,5-Stilbenediol
trans-3,5-Dihydroxystilbene
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 22139-77-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 881R434AIB
| PubChem = 5280457
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 101506
| SMILES = C1=CC=C(C=C1)\C=C\C2=CC(=CC(=C2)O)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4444110
| InChI = 1/C14H12O2/c15-13-8-12(9-14(16)10-13)7-6-11-4-2-1-3-5-11/h1-10,15-16H/b7-6+
| InChIKey = YCVPRTHEGLPYPB-VOTSOKGWBH
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C14H12O2/c15-13-8-12(9-14(16)10-13)7-6-11-4-2-1-3-5-11/h1-10,15-16H/b7-6+
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = YCVPRTHEGLPYPB-VOTSOKGWSA-N
}}
|Section2={{Chembox Properties
| C=14 | H=12 | O=2
| Appearance = white solid
| Density =
| MeltingPtC = 153 to 155
| MeltingPt_notes =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
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Pinosylvin is an organic compound with the formula C6H5CH=CHC6H3(OH)2. A white solid, it is related to trans-stilbene, but with two hydroxy groups on one of the phenyl substituents. It is very soluble in many organic solvents, such as acetone.{{Cite book|title=CRC Handbook of Chemistry and Physics, 95th Edition|last=M.|first=Haynes, William|date=2014|publisher=CRC Press|isbn=9781482208689|edition= 95th |location=Hoboken|pages=458|chapter=3|oclc=908078665}}
Occurrence
Pinosylvin is produced in plants in response to fungal infections, ozone-induced stress, and physical damage for example.{{Cite journal|last1=Hovelstad|first1=Hanne|last2=Leirset|first2=Ingebjorg|last3=Oyaas|first3=Karin|last4=Fiksdahl|first4=Anne|date=2006-01-31|title=Screening analyses of pinosylvin stilbenes, resin acids and lignans in Norwegian conifers|journal=Molecules (Basel, Switzerland)|volume=11|issue=1|pages=103–114|issn=1420-3049|pmid=17962750|doi=10.3390/11010103|citeseerx=10.1.1.599.4403|pmc=6148674 |doi-access=free }} It is a fungitoxin protecting the wood from fungal infection.{{Cite journal|last1=Lee|first1=S. K.|last2=Lee|first2=H. J.|last3=Min|first3=H. Y.|last4=Park|first4=E. J.|last5=Lee|first5=K. M.|last6=Ahn|first6=Y. H.|last7=Cho|first7=Y. J.|last8=Pyee|first8=J. H.|date=March 2005|title=Antibacterial and antifungal activity of pinosylvin, a constituent of pine|journal=Fitoterapia|volume=76|issue=2|pages=258–260|doi=10.1016/j.fitote.2004.12.004|issn=0367-326X|pmid=15752644}} It is present in the heartwood of Pinaceae and also found in Gnetum cleistostachyum.{{Cite journal|last1=Yao|first1=Chun-Suo|last2=Lin|first2=Mao|last3=Liu|first3=Xin|last4=Wang|first4=Ying-Hong|date=April 2005|title=Stilbene derivatives from Gnetum cleistostachyum|journal=Journal of Asian Natural Products Research|volume=7|issue=2|pages=131–137|doi=10.1080/10286020310001625102|issn=1028-6020|pmid=15621615}}
Injected in rats, pinosylvin undergoes rapid glucuronidation and a poor bioavailability.{{Cite journal|last1=Roupe|first1=Kathryn A.|last2=Yáñez|first2=Jaime A.|last3=Teng|first3=Xiao Wei|last4=Davies|first4=Neal M.|date=November 2006|title=Pharmacokinetics of selected stilbenes: rhapontigenin, piceatannol and pinosylvin in rats|journal=The Journal of Pharmacy and Pharmacology|volume=58|issue=11|pages=1443–1450|doi=10.1211/jpp.58.11.0004|issn=0022-3573|pmid=17132206|doi-access=free}}
Biosynthesis
Pinosylvin synthase, an enzyme, catalyzes the biosynthesis of pinosylvin from malonyl-CoA and cinnamoyl-CoA:
:3 malonyl-S-CoA + cinnamoyl-S-CoA → 4 CoA-SH + pinosylvin + 4 CO2
This biosynthesis is noteworthy because plant biosyntheses employing cinnamic acid as a starting point are rare compared to the more common use of p-coumaric acid. Two other compounds produced from cinnamic acid are anigorufone and curcumin.{{Cite journal|last1=Schmitt|first1=B.|last2=Hölscher|first2=D.|last3=Schneider|first3=B.|date=February 2000|title=Variability of Phenylpropanoid PBiosynthesis of Phenylphenalenones in Anigozanthos preissii|journal=Phytochemistry|volume=53|issue=3|pages=331–337|issn=0031-9422|pmid=10703053|doi=10.1016/s0031-9422(99)00544-0}}{{Cite journal|last1=Kita|first1=Tomoko|last2=Imai|first2=Shinsuke|last3=Sawada|first3=Hiroshi|last4=Kumagai|first4=Hidehiko|last5=Seto|first5=Haruo|date=July 2008|title=The Biosynthetic Pathway of Curcuminoid in Turmeric (Curcuma longa) as Revealed by 13C-Labeled Precursors|journal=Bioscience, Biotechnology, and Biochemistry|volume=72|issue=7|pages=1789–1798|doi=10.1271/bbb.80075|issn=1347-6947|pmid=18603793|doi-access=free}}