Entry Name: Fulvic acid
Synonym(s): 4,10-Dihydro-3,7,8-trihydroxy-3-methyl-10-oxo-1H,3H-pyrano[4,3-b][1]benzopyran-9-carboxylic acid, 9CI.
CRC Number: BFG52-M
CAS Registry Number: 479-66-3
Type of Compound Code(s): VI0070  ZG3000 
Molecular Formula: C14H12O8
Molecular Weight: 308.244
Accurate Mass: 308.05322
Percentage Composition: C 54.55%; H 3.92%; O 41.52%
Biological Source: Metab. of Penicillium spp.
Physical Description: Yellow cryst.
Melting Point: Mp 246°   dec.   
UV: [neutral]λmax315;342 ( dioxan)
InChi Key: FCYKAQOGGFGCMD-UHFFFAOYSA-N
InChi: InChI=1S/C14H12O8/c1-14(20)3-8-5(4-21-14)11(16)9-7(22-8)2-6(15)12(17)1
0(9)13(18)19/h2,15,17,20H,3-4H2,1H3,(H,18,19)

Derivative: 7-Me ether
Synonym(s): 7-O-Methylfulvic acid.
CRC Number: HOK01-P
CAS Registry Number: 114992-37-9
Type of Compound Code(s): ZG3000  VI0070 
Molecular Formula: C15H14O8
Molecular Weight: 322.271
Accurate Mass: 322.06887
Percentage Composition: C 55.90%; H 4.38%; O 39.72%
Biological Source: Prod. by Penicillium brefeldianum
Physical Description: Yellow oil
UV: [neutral]λmax225;315 ( MeOH)
InChi Key: OIQRCBINTJVAGZ-UHFFFAOYSA-N
InChi: InChI=1S/C15H14O8/c1-15(20)4-9-6(5-22-15)12(16)10-7(23-9)3-8(21-2)13(1
7)11(10)14(18)19/h3,17,20H,4-5H2,1-2H3,(H,18,19)

Derivative: 3-Deoxy, 3,4-didehydro
Synonym(s): 7,8-Dihydroxy-3-methyl-10-oxo-1H,10H-pyrano[4,3-b][1]benzopyran-9-carboxylic acid, 9CI. Anhydrofulvic acid.
CRC Number: HOK00-O
CAS Registry Number: 95730-85-1
Type of Compound Code(s): ZG3000  VI0070 
Molecular Formula: C14H10O7
Molecular Weight: 290.229
Accurate Mass: 290.042655
Percentage Composition: C 57.94%; H 3.47%; O 38.59%
Biological Source: Prod. by Penicillium afacidum, Penicillium glabrum, marine-derived Penicillium striatisporum and a Paecilomyces sp. C65
Biological Use / Importance: Antifungal agent. Collagenase inhibitor
Physical Description: Yellow prisms (DMF aq.)
Melting Point: Mp 237  -  242°     
InChi Key: QECRRBWJXIZNNN-UHFFFAOYSA-N
InChi: InChI=1S/C14H10O7/c1-5-2-8-6(4-20-5)12(16)10-9(21-8)3-7(15)13(17)11(10
)14(18)19/h2-3,15,17H,4H2,1H3,(H,18,19)

Derivative: 3-Deoxy, 3,4-didehydro, 7-Me ether
Synonym(s): 7-O-Methylanhydrofulvic acid.
CRC Number: HOK02-Q
CAS Registry Number: 95730-84-0
Type of Compound Code(s): VI0070  ZG3000 
Molecular Formula: C15H12O7
Molecular Weight: 304.256
Accurate Mass: 304.058305
Percentage Composition: C 59.22%; H 3.98%; O 36.81%
Biological Source: Prod. by Penicillium brefeldianum
Physical Description: Oil
UV: [neutral]λmax212;286 ( MeOH)
InChi Key: OGCNEBYUWVVLMZ-UHFFFAOYSA-N
InChi: InChI=1S/C15H12O7/c1-6-3-8-7(5-21-6)13(16)11-9(22-8)4-10(20-2)14(17)12
(11)15(18)19/h3-4,17H,5H2,1-2H3,(H,18,19)

Derivative: 3-Deoxy, 3,4-didehydro, 8-Me ether
Synonym(s): 8-O-Methylanhydrofulvic acid.
CRC Number: PKD54-G
CAS Registry Number: 959634-79-8
Type of Compound Code(s): VI0070  ZG3000 
Molecular Formula: C15H12O7
Molecular Weight: 304.256
Accurate Mass: 304.058305
Percentage Composition: C 59.22%; H 3.98%; O 36.81%
Biological Source: Prod. by the marine-derived Penicillium striatisporum MST-F9530
Physical Description: Yellow oil
UV: [neutral]λmax210 (ε2600) ;258 (ε2900) ;312 (ε7400) ( MeOH)
InChi Key: ZUGRMYDIGDDWDI-UHFFFAOYSA-N
InChi: InChI=1S/C15H12O7/c1-6-3-9-7(5-21-6)13(17)11-10(22-9)4-8(16)14(20-2)12
(11)15(18)19/h3-4,16H,5H2,1-2H3,(H,18,19)

References:
Oxford, A.E.  et al., Biochem. J., 1935, 29, 1102  (isol)
Dean, F.M.  et al., Nature (London), 1957, 179, 366  (struct)
Kurobane, I.  et al., Tet. Lett., 1981, 493  (biosynth)
Yamauchi, M.  et al., Chem. Comm., 1983, 335; 1984, , 1505; 1984, , 1565  (synth)
Katayama, S.  et al., Heterocycles, 1985, 23, 227  (synth)
Yamauchi, M.  et al., JCS Perkin 1, 1987, 389  (synth)
Demetriadou, A.K.  et al., JCS Perkin 1, 1988, 773- 778  (7-O-methyl derivs)
Fujita, K.-I.  et al., J. Antibiot., 1999, 52, 628- 634  (Anhydrofulvic acid)
Wang, J.-F.  et al., Acta Cryst. E, 2003, 59, o1244- o1245  (Anhydrofulvic acid, cryst struct)
Capon, R.J.  et al., J. Nat. Prod., 2007, 70, 1746- 1752  (marine, isol)


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