(2E,6E)-farnesol





Description


Farnesol is an acyclic sesquiterpenoid alcohol with industrial and medical potential. In plant systems, farnesol is synthesized from farnesyl diphosphate (FPP) via farnesol synthase [262]. In microbial production platforms, farnesol biosynthesis is achieved by augmenting the intracellular pool of the C15 precursor farnesyl diphosphate (FPP) [261, 262]. Precursor supply is enhanced through the expression of a heterologous mevalonate (MVA) pathway to produce isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), coupled with the overexpression of FPP synthase (encoded by ispA) [261, 262]. Downstream dephosphorylation of accumulated FPP to farnesol can be driven by integral membrane phosphatases possessing moonlight FPP hydrolysis activity, specifically phosphatidylglycerophosphatase B (PgpB) and undecaprenyl diphosphate phosphatase (YbjG) [262]. Mutational analysis reveals that conserved active-site residues, including H207 in PgpB and H145 in YbjG, are critical for executing this FPP cleavage [262].


Chemical Formula:
C15H26O
Molecular Weight:
222.37 Daltons
Monoisotopic Mass:
222.1983654567 Daltons
SMILES:
CC(C)=CCCC(C)=CCCC(C)=CCO
InChI:
1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9+,15-11+

Synonyms
  • (E,E,)-farnesol
  • (E,E,)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol
  • 2-trans-S-6-trans-farnesol
  • 2-trans,6-trans-farnesol
  • all-trans farnesol
  • FOH

Databases
HMDB:  HMDB04305
LIPID MAPS:  LMPR0103010001
ChemSpider:  392816
ChEBI:  16619
PubChem (CID):  445070
KEGG:  C01126
RefMet:  2E,6E-Farnesol
MetaNetX:  MNXM1161
CAS:  106-28-5
PupChem (SID):  4357
CHEMBL:  CHEMBL25308
LIPIDBANK:  IIP0051
KNApSAcK:  C00003132 C00035092
PDB-CCD:  FOF
3DMET:  B00244
NIKKAJI:  J5.049K