MONO-OXYGENATED STEARIC ACIDS AND PRIMARY AMIDES
675
tallization from ethyl acetate at about 35°C and subjected to
GC–MS analysis.
4. Wallen, L.L., R.G. Benedict, and R.W. Jackson, The Microbio-
logical Production of 10-Hydroxystearic Acid from Oleic Acid,
Arch. Biochem. Biophys. 99:249–253 (1962).
Neither of the mass spectra of the purified products dis-
played significant molecular ion peaks. Both spectra showed
strong characteristic primary amide peaks at m/z 59 and 72, re-
sulting from McLafferty rearrangement and γ-cleavage, respec-
tively (18). The spectrum of the 10-HSA product displayed
prominent peaks at m/z 157 and 186. These fragments are con-
sistent with cleavage on either side of the hydroxyl group (19).
The spectrum also contained an abundant ion at m/z 169, pos-
sibly due to further decomposition of the m/z 186 peak by the
loss of ammonia, analogous to the loss of methanol from
methyl esters described by Murphy (19). In addition to the
characteristic primary amide peaks, the spectrum of the 10-
KSA product displayed a base peak at m/z 142, which was
likely the result of β-cleavage to the keto group (19). Other
peaks present in the spectrum at m/z 156 and 199 were consis-
tent with McLafferty rearrangement ions resulting from cleav-
age on either side of the carbonyl group, while α-cleavage to
5
. Litchfield J.H., and G.E. Pierce, Microbiological Synthesis of
Hydroxy-Fatty Acids and Keto-Fatty Acids, U.S. Patent
4,582,804 (1986).
6. Davis, E.N., L.L. Wallen, J.C. Goodwin, W.K. Rohwedder, and
R.A. Rhodes, Microbial Hydration of cis-9-Alkenoic Acids,
Lipids 4:356–362 (1969).
7
. Koritala, S., L. Hosie, C.T. Hou, C.W. Hesseltine, and M.O.
Bagby, Microbial Conversion of Oleic Acid to 10-Hydroxys-
tearic Acid, Appl. Microbiol. Biotechnol. 32:299–304 (1989).
8. Kuo, T.M., T. Kaneshiro, and C.T. Hou, Microbiological Con-
versions of Fatty Acids to Value-Added Products, in Lipid
Biotechnology, edited by T.M. Kuo and H.W. Gardner, Marcel
Dekker, New York, 2002, pp. 605–628.
9
. Kaneshiro, T., J.K. Huang, D. Weisleder, and M.O. Bagby,
10(R)-Hydroxystearic Acid Production by a Novel Microbe,
NRRL B-14797, Isolated from Compost, J. Ind. Microbiol.
1
3:351–355 (1994).
1
0. Kuo, T.M., L.K. Nakamura, and A.C. Lanser, Conversion of
Fatty Acids by Bacillus sphaericus-like Organisms, Curr. Mi-
crobiol. 45:265–271 (2002).
each side of the carbonyl would result in peaks seen at m/z 141 11. Lanser, A.C., Conversion of Oleic Acid to 10-Ketostearic Acid
and 184 (19). The results indicated the formation of 10-hydrox-
ystearamide and 10-ketostearamide, respectively, by lipase-cat-
alyzed direct amidation of 10-HSA and 10-KSA.
The melting point of 10-hydroxystearamide and 10-ke-
tostearamide were 115 and 120°C, respectively. Both were sub-
stantially higher than their corresponding free FA of 84 and
by a Staphylococcus Species, J. Am. Oil Chem. Soc. 70:543–545
1993).
2. Difco Laboratories, DIFCO Manual, 10th edn., Difco Laborato-
ries, Detroit, 1984, p. 679.
3. Kuo, T.M., K.J. Ray, and L.K. Manthey, A Facile Reactor
Process for Producing 7,10-Dihydroxy-8(E)-octadecenoic Acid
from Oleic Acid Conversion by Pseudomonas aeruginosa,
Biotechnol. Lett. 25:29–33 (2003).
(
1
1
83°C. This could make the newly prepared fatty amides useful
1
1
1
1
4. Kuo, T.M., and G. Knothe, Production and Properties of
in the formulation of special lubrication applications.
7
,10,12-Trihydroxy-8(E)-octadecenoic Acid from Ricinoleic
Acid Conversion by Pseudomonas aeruginosa, Eur. J. Lipid
Technol. 106:405–411 (2004).
ACKNOWLEDGMENTS
5. Levinson, W.E., T.M. Kuo, and D. Weisleder, Characterization
of Primary Fatty Amides Produced by Lipase-Catalyzed Ami-
dation of Hydroxylated Fatty Acids, J. Am. Oil Chem. Soc.
We thank Karen Ray and Mark Hocking for excellent technical as-
sistance, Karen Ray and Dr. Lawrence Nakamura for helpful discus-
sion during the study, and Trina Hartman and Dr. Neil Price for mass
spectral analysis. Names are necessary to report factually on avail-
able data; however, the USDA neither guarantees nor warrants the
standard of the product, and the use of the name by USDA implies
no approval of the product to the exclusion of others that may also
be suitable.
8
2:501–504 (2005).
6. Litjens, M.J.J., A.J.J. Straathof, J.A. Jongejan, and J.J. Heijnen,
Exploration of Lipase-Catalyzed Direct Amidation of Free Car-
boxylic Acids with Ammonia in Organic Solvents, Tetrahedron
5
5:12411–12418 (1999).
7. Litjens, M.J.J., A.J.J. Straathof, J.A. Jongejan, and J.J. Heijnen,
Synthesis of Primary Amides by Lipase-Catalyzed Amidation
of Carboxylic Acids with Ammonium Salts in an Organic Sol-
vent, Chem. Commun. 13:1255–1256 (1999).
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[Received December 20, 2005; accepted May 24, 2006]
JAOCS, Vol. 83, no. 8 (2006)