Synthesis of cis-12,13-epoxy-cis-9-octadecenol and 12(13)-hydroxy-cis-9-octadecenol from vernonia oil using lithium aluminum hydride

Article abstract of DOI:10.1007/s11746-000-0139-9

Reduction of vernonia oil methyl esters (VOME) into epoxy fatty alcohol and diols was achieved with lithium aluminum hydride (LAH), under reflux and room temperature conditions, by using hexane and tetrahydrofuran (THF) as solvents. The reactions of VOME with LAH in hexane produced cis-12,13-epoxy-cis-9-octadecenol as a major product with an isolated yield of 73.62%, whereas the reactions with LAH in THF gave isomers of 12(13)-hydroxy-cis-9-octadecenol as the major products with an isolated yield of 95.1%. LAH was similarly reacted with vernonia oil (VO) to give the same products in lower yields, ¹H nuclear magnetic resonance (NMR), ¹³C NMR, gas chromatography-mass spectrometry, and infrared were used to characterize these products. This study demonstrates the ability to control the reactivity of the epoxy functionality in VO or VOME with the choice of polar or nonpolar solvents, and extends the range of oleochemicals that can be derived from vernonia oil.

Full text of DOI:10.1007/s11746-000-0139-9

Synthesis of cis-12,13-Epoxy-cis-9-octadecenol
and 12(13)-Hydroxy-cis-9-octadecenol
from Vernonia Oil Using Lithium Aluminum Hydride
Eisa B. Elhilo, Melissa A. Anderson, and Folahan O. Ayorinde*
Department of Chemistry, Howard University, Washington, DC 20059
from the LAH reduction of tripalmitin and triolein, olive oil,
lard, and oil of chaulmoogra glycerides. In another study,
Walborsky and Colombini (7) reported on the syntheses of al-
cohol mixtures by the LAH reduction of glycidic esters.
Ernest and coworkers (8,9) have also demonstrated the ability
of LAH to reduce epoxides to alcohols.
ABSTRACT: Reduction of vernonia oil methyl esters (VOME)
into epoxy fatty alcohol and diols was achieved with lithium
aluminum hydride (LAH), under reflux and room temperature
conditions, by using hexane and tetrahydrofuran (THF) as sol-
vents . The reactions of VOME with LAH in hexane produced
cis-12,13-epoxy-cis-9-octadecenol as a major product with an
isolated yield of 73.62%, whereas the reactions with LAH in
THF gave isomers of 12(13)-hydroxy-cis-9-octadecenol as the
major products with an isolated yield of 95.1%. LAH was simi-
larly reacted with vernonia oil (VO) to give the same products
Therefore, we were interested in studying the reaction be-
tween LAH and vernonia oil (VO), which is a naturally epoxi-
dized vegetable oil (10). The products from this reaction could
constitute potential intermediates in the synthesis of oleochem-
icals from Vernonia galamensis seed oil, since it has been rec-
ognized as a potential oil seed crop (11,12). The initial interest
was due to the unique fatty acid composition of its seed oil,
which contains epoxidized triacylglycerols, of which triverno-
lin has been shown to be the major triacylglycerol (13,14).
Previous work in our laboratory indicated that the epoxy
functionality in VO was reactive toward nucleophilic reagents
only under acidic conditions (12), whereas aminolysis (15) of
the oil gave epoxy-containing amides with no indication of
epoxy opening. Also, the base-catalyzed methanolysis (14) of
the oil resulted only in transesterification to give epoxidized
methyl ester. Consequently, we were interested in studying
the effect of a nucleophilic agent such as LAH on the epoxy
functionality. Therefore, as part of an ongoing research effort
we investigated the reaction of VO with LAH with a particu-
lar focus on the reactivity of its epoxy functionality under dif-
ferent reaction conditions of temperature and solvents. In this
paper we report the effect of temperature and solvent on the
reactions that involved LAH/VO and LAH/vernonia oil
methyl esters (VOME) to give an epoxy alcohol and diols.
1
in lower yields. H nuclear magnetic resonance (NMR), 13C
NMR, gas chromatography–mass spectrometry, and infrared
were used to characterize these products.
This study demonstrates the ability to control the reactivity
of the epoxy functionality in VO or VOME with the choice of
polar or nonpolar solvents, and extends the range of oleochem-
icals that can be derived from vernonia oil.
Paper no. J9458 in JAOCS 77, 873–878 (August 2000).
KEY WORDS: 13C NMR, cis-12,13-epoxy-cis-9-octadecenol,
GC–MS, 1H NMR, 12(13)-hydroxy-cis-9-octadecenol, IR, ver-
nonia oil, vernonia oil methyl esters.
The most extensively used oleochemicals, after fatty acids,
are fatty alcohols, and there are growing efforts aimed at de-
veloping new derivatives and applications for the alcohols
(1). Current laboratory methodology for their synthesis in-
volves direct reduction of fatty esters with lithium aluminum
hydride (LAH) (2). LAH is among the most powerful com-
plex metal hydride reducing agents, with the ability to reduce
carbonyl functionality in aldehydes, ketones, and esters to
corresponding alcohols, while leaving the carbon-carbon dou-
ble bond or carbon-carbon triple linkages untouched (3–5). In
the case of the reaction of LAH with esters (2), the reduction
of the ester functionality proceeds by nucleophilic attack of
the hydride ion on the carbonyl group, leading to the forma-
tion of intermediate alkoxide salts from which the alcohol is
generated upon acidification. Micovic and coworkers (6) re-
ported on the production of corresponding alcohols resulting
EXPERIMENTAL PROCEDURES
Reagents. The crude VO used in this study was obtained from
International Exchange of Trade and Technology, Inc. (Cul-
ver, IN). Transesterification of VO with sodium methoxide
yielded the VOME. Lithium aluminum hydride, hexane,
tetrahydrofuran (THF), and methyl alcohol were purchased
from Aldrich Chemicals Inc. (Milwaukee, WI).
Instrumentation. Reactions and products were monitored
with a Hewlett-Packard 5890 series II gas chromatograph
(Avondale, PA) coupled with a Hewlett-Packard 5989A mass
*To whom correspondence should be addressed at Department of Chemistry,
Howard University, 525 College Street, NW, Washington, DC 20059.
E-mail: fayorinde@howard.edu
Copyright © 2000 by AOCS Press
873
JAOCS, Vol. 77, no. 8 (2000)

874
E.B. ELHILO ET AL.
spectrometer. The interface oven and transfer line were main- showed the molecular ion at m/z 282, and a diagnostic ion at
tained at 285°C, the ionizer temperature setting was at 150°C, m/z 264 (M − H2O).
using electron impact (EI) mode, with electron energy at 70
LAH reaction with VOME in THF. This reaction was per-
eV. High-resolution capillary gas chromatography was con- formed under the same conditions as above, except that THF
ducted with a Supelco fused-silica SPB-I (30 m, 0.32 mm in- was used as solvent and the reaction was allowed to continue
side diameter, 0.25 µm film) column (Bellefonte, PA), oven for 7 h. The resulting filtrate was stripped with a rotary evap-
temperature was programmed from 50 to 300°C, and helium orator to give 2.24 g (97.80%) of a crude product that con-
was used as the carrier gas with a head pressure of 10 psi. tained isomers of (12)13-hydroxy-cis-9-octadecenol (diol) as
Characterization of alcohols by gas chromatography–mass major products and hexadecanol, cis-9,12-octadecadienol,
spectrometry (GC–MS) was performed by dissolving a 10-mg cis-9-octadecenol, and octadecanol as minor products. The
sample of alcohol in 2 mL methylene chloride, from which 1 crude product was analyzed by FTIR to give hydroxy absorp-
µL was injected on the column. The infrared (IR) spectra tion at 3334.6 cm−1. The MS (EI) data of the diols showed di-
were obtained on a PerkinElmer model 1600-Infrared Spec- agnostic ions at m/z 266 (M − H2O) and m/z 248 (M − 2H2O).
trophotometer (Norwalk, CT). Solid samples were run with
LAH reaction with VO under reflux conditions (in hexane
KBr, while liquid samples were run neat. The 13C nuclear or THF). To a 500-mL, three-neck, round-bottomed flask
magnetic resonance (13C NMR) and proton nuclear magnetic equipped with water condenser, separatory funnel, and mag-
resonance (1H NMR) spectra were recorded on a GE-NMR netic stirring bar, 90 mL of solvent (hexane or THF) and 1.8
QE-300 model spectrometer (Fremont, CA) with chloro- g (0.047 mol) LAH were added. Through the separatory fun-
form-d (CDCl3) as solvent and source of internal standard.
nel, 2.5 g (0.0027 mol) of VO was added with stirring. The
Transesterification of VO to give VOME. VO (24.85 g, separatory funnel was rinsed with 10 mL of the solvent, and
0.08 mol) was transferred into a 500-mL round-bottomed the rinse was added to the mixture in the flask. The reaction
flask. Hexane (125 mL) was added, followed by 12.5 mL mixture was then stirred continuously for 24 h under reflux,
sodium methoxide in methanol (25 wt%). The flask was fit- after which 5 mL water was slowly added. The mixture was
ted onto a rotary evaporator, and then allowed to rotate (ap- further stirred for 15 min and then vacuum-filtered. The reac-
proximately 240 revolutions/min) for about 80 min without tion flask was rinsed with 10 mL of the solvent and again the
heat or vacuum. The resulting mixture was transferred into a rinse was added to the Buchner funnel. The filtrate was
separatory funnel and 125 mL water was added. The flask was stripped with a rotary evaporator to produce 1.75 g (76.75%)
rinsed with approximately 20 mL water, and the rinse was of a crude product (with hexane as solvent) that contained cis-
added to the separatory funnel. The hexane layer was drawn 12,13-epoxy-cis-9-octadecenol (epoxy alcohol) as a major
off, and then stripped to give 24.51g (98.2% yield, based on product and hexadecanol, cis-9,12-octadecadienol, cis-9-oc-
methyl vernolate) of VOME. GC analysis indicated a mixture tadecenol, and octadecanol as minor products. The crude
of methyl palmitate, methyl stearate, methyl oleate, methyl product was analyzed by FTIR to give hydroxy absorption at
linoleate, and methyl vernolate. MS diagnostic ions for methyl 3433.8 cm−1 and absorptions at 820.6 and 840.0 cm−1 (epoxy
vernolate (m/z) were: 292 (M − H2O) and 279 (M − OCH3) and group). The MS (EI) data of the epoxy alcohol showed the
for 13C NMR data (ppm), 173.49 (C=O), 132.03, 123.83 molecular ion at m/z 282, and diagnostic ion at m/z 264
(CH=CH), 56.59, 55.98 (epoxy carbons), and 50.87 (OCH3).
(M − H2O). The reaction in THF gave 2.00 g (86.96%) of the
LAH reaction with VOME in hexane. To a 500-mL, three- crude product, which contained isomers of (12)13-hydroxy-
neck, round-bottomed flask equipped with an air condenser, cis-9-octadecenol (diol) as major products and hexadecanol,
separatory funnel, and magnetic stirring bar, 60 mL hexane cis-9,12-octadecadienol, cis-9-octadecenol, and octadecanol
and 0.9 g (0.024 mol) LAH were added. Through the separa- as minor products. Details of the isolation and further charac-
tory funnel, 2.5 g (0.008 mol) of VOME was added with stir- terization of the epoxy alcohol and diols are provided below.
ring. The separatory funnel was rinsed with 10 mL hexane
Isolation of cis-12,13-epoxy-cis-9-octadecenol (epoxy al-
and the rinse was added to the mixture in the flask. The reac- cohol). The crude products from VOME/LAH, and VO/LAH
tion mixture was then stirred continuously for 2 h at room reactions in hexane were dissolved separately in 50 mL
temperature, after which 5 mL water was slowly added. The hexane and the solution was cooled with ice/water (about
mixture was further stirred for 15 min and then vacuum-fil- 5°C) for 1 h. After crystallization, the solution was vacuum-
tered. The reaction flask was rinsed with 10 mL hexane and filtered to obtain white crystals (epoxy alcohol) and a filtrate
the rinse was added to the Buchner funnel. The filtrate was containing the remainder of the fatty alcohols. The white
stripped with a rotary evaporator to give 2.14 g (94.30%) of a crystals were allowed to dry to give 1.4 g (76.92%) of pure
crude product that contained cis-12,13-epoxy-cis-9-octade- epoxy alcohol from VOME/LAH, and 0.72 g (39.34%) of
cenol (epoxy alcohol) as a major product and hexadecanol, pure epoxy alcohol from VO/LAH. IR data (cm−1): 3298.3
cis-9,12-octadecadienol, cis-9-octadecenol, and octadecanol (OH), 820.6, 846.0 (epoxy group). MS data (m/z): 282 (M+.)
as minor products. The crude product was analyzed by and 264 (M − H2O). 1H NMR data (ppm): 5.35–5.60 (CH=CH),
Fourier transform infrared (FTIR), which gave hydroxy ab- 3.64 (O–CH2), 2.90 (O–C–H of epoxide), 2.00–2.45
sorption at 3298.3 cm−1 and absorptions at 820.6 and 846.0 (CH2–CH=CH–CH2), 1.25–1.75 (CH2)n, and 0.90 (CH3).
cm−1 (epoxy group). The MS (EI) data of the epoxy alcohol 13C NMR data (ppm): 132.481 and 123.697 (C=C), 56.461
JAOCS, Vol. 77, no. 8 (2000)

LITHIUM ALUMINUM HYDRIDE REDUCTION OF VERNONIA OIL
875
and 57.107 (Cs of epoxide), 62.597 (C–OH), 22.424–32.596 ever, in this case, there was a greater time differential, the re-
(CH2)n, and 13.801 (CH3). flux reaction was complete in 1 h, and the room temperature
Isolation of 12(13)-hydroxy-cis-9-octadecenol (diol). The reaction was complete in 7 h. The greater time differential
crude products from VOME/LAH and VO/LAH reactions in could be due to the possibility that ring opening of the epoxy
THF were dissolved separately in 100 mL of MeOH/H2O functionality requires greater energy.
(4:1, vol/vol ratio) and the solution was transferred to a sepa-
We propose that the difference in the outcome of these re-
ratory funnel and then extracted with 25 mL hexane (×4). The actions could be due to the solubility of the intermediate
aqueous layer containing pure diol was separated, and the alkoxide salt that is formed during the LAH reduction of the
four hexane portions were combined. Then the combination esters. Thus any subsequent reactions, such as epoxy ring
of hexane portions was extracted twice with 25 mL of opening, depend on the solubility of this intermediate salt.
MeOH/H2O (4:1, vol/vol ratio). All the aqueous layers were When THF (the more polar solvent) was used, there was ring
combined, washed with 10 mL hexane, and then stripped with opening due to the higher solubility of the intermediate
a rotary evaporator to give 1.74 g (95.1%) of pure diol iso- lithium alkoxide. This conclusion was supported by the fact
mers from VOME/LAH, and 1.5 g (81.5%) of pure diol iso- that all the reactions were monitored by IR spectroscopy,
mers from VO/LAH. IR data (cm−1): 3334.5 (OH). Both iso- which indicated complete disappearance of the ester carbonyl
mers showed similar MS data with the following diagnostic prior to the reduction of the epoxy functionality when THF
ions (m/z): 266 (M − H2O) and 248 (M − 2H2O).1H-NMR was used as the solvent.
data (ppm): 5.35–5.60 (CH=CH), 3.60 (O–CH2), 2.65 (OH),
The GC–MS of the VOME/LAH reaction in hexane at
2.00– 2.193 (CH2 attached to CH=CH), 1.30–1.75 (CH2)n, room temperature and under reflux indicated a chromatogram
and 0.850 (CH3). 13C NMR data (ppm): 132.739, 130.188, with a mixture of epoxy alcohol (cis-12,13-epoxy-cis-9-
129.154 and 125.118 (C=C) of the isomers, 71.349 (C at- octadecenol), hexadecanol, cis-9,12-octadecadienol, cis-9-
tached to terminal OH), 62.403 and 62.113 (C12 and C13 at- octadecenol, and octadecanol. The mass spectrum of the
tached to OH), 37.150–22.424 (CH2)n, and 13.866 (CH3).
epoxy alcohol showed the normal alkene-type fragmentation
due to the loss of water, with a molecular ion at m/z 282, and
a fragment ion at m/z 264 (M − H2O).
RESULTS AND DISCUSSION
The GC-MS of the VOME/LAH reactions in THF at room
Table 1 shows the reaction outcome of LAH reduction of VO temperature and reflux also indicated a chromatogram with a
and VOME under different reaction conditions. All the reac- mixture of diol isomers 12(13)-hydroxy-cis-9-octadecenol,
tion completions were monitored by the disappearance of the hexadecanol, cis-9,12-octadecadienol, cis-9-octadecenol, and
ester carbonyl absorption in the IR spectra. The reduction of octadecanol. The mass spectrum of each of the diols showed
VO in hexane under reflux was incomplete, and hence it gave diagnostic ions at m/z 266 (M − H2O) and m/z 248 (M − 2H2O).
poor yield; however, all other reactions went to completion.
LAH reactions with VO in hexane and in THF. The ver-
LAH reactions with VOME in hexane and in THF. The re- nonia oil experiments provided a direct reduction of the tri-
actions of VOME/LAH in hexane were performed at room acylglycerols to the corresponding fatty alcohols without the
temperature and under reflux. Both sets of experiments intermediary methyl esters. The reactions were additionally
yielded similar results except that the reaction under reflux monitored with GC–MS every 6 h using farnesol (3,7, and 11-
was complete in 1 h, whereas the reaction at room tempera- trimethyl-2,6,10 dodecatrien 1-ol) as the internal reference.
ture was complete in 2 h. These reactions resulted in the Reaction under reflux in hexane produced the epoxy alcohol
epoxy alcohol (cis-12,13-epoxy-cis-9-octadecenol) as a major (cis-12,13-epoxy-cis-9-octadecenol) as a major product,
product, and there was no evidence of epoxy ring opening. which was confirmed by GC–MS, while the reaction under
On the other hand, the reactions of VOME/LAH in THF at reflux in THF produced the diol isomers [12(13)-hydroxy-cis-
room temperature and under reflux gave the diol alcohols, 9-octadecenol] as major products, which was also confirmed
12(13)-hydroxy-cis-9-octadecenol as major products. How- by GC-MS. Attempts at performing these reactions at room
TABLE 1
Lithium Aluminum Hydride (LAH) Reduction of Vernonia Oil (VO) and Vernonia Oil Methyl Esters (VOME) to Give Epoxy Alcohol and Diols
Substrate
used
Solvent
used
Ester redn.b
to alcohol
Epoxy ring
opening
Reaction
condition
Reaction
time (h)
Yield of
crude (%)
Isolated
producta (%)
VOME
VOME
VOME
VOME
VO
Hexane
Hexane
THFb
THF
Hexane
THF
Yes
Yes
Yes
Yes
Yes
Yes
No
No
Yes
Yes
No
Yes
RTb
Reflux
RT
Reflux
Reflux
Reflux
2
1
7
1
24
24
94.30
90.75
97.80
98.70
76.75
86.96
76.92
73.62
95.10
96.72
39.34
81.52
VO
aBased on 80% vernolate in VOME.
bRedn., reduction; RT, room temperature; THF, tetrahydrofuran.
JAOCS, Vol. 77, no. 8 (2000)

876
E.B. ELHILO ET AL.
FIG. 1. 13C nuclear magnetic resonance (NMR) spectrum of the epoxy alcohol. Chemical shifts (ppm): 132.481 and
123.697 (CH=CH), 56.461 and 57.107 (epoxy carbons, O–C–H), 62.597 carbon attached to the hydroxyl group,
22.424–32.596 (CH2)n, and 13.801 (CH3).
temperature were abandoned because of the prolonged reac- and 57.107, carbon attached to the hydroxyl group (C–OH) at
tion completion time. 62.597, methylene carbons (CH2)n at 22.424–32.596, and
NMR analysis. The 1H NMR data from the epoxy alcohol methyl carbon (CH3) at 13.801. The 1H NMR data from the
indicated the presence of the olefinic protons (CH=CH) at diol mixture indicated the presence of the olefinic protons
5.35 and 5.60, methylene protons (O–CH2) at 3.64, epoxy (CH=CH) at 5.35 and 5.60, methylene and methyne protons
protons (O–C–H) at 2.9, protons of methylene attached to (CH2–OH and CH–OH) at 3.60, protons of the methylene at-
olefinic group (–CH2–CH=CH–CH2–) at 2.00–2.45, protons tached to olefinic group (–CH2–CH=CH–CH2–) at 2.01–2.62,
of other methylene groups (CH2)n at1.25–1.76, and protons protons of the hydroxyl groups (OH) at 2.65, protons of other
of methyl (CH3) groups at 0.90. 13C NMR data (Fig. 1) methylene groups (CH2)n 1.30–1.75, and protons of methyl
showed the olefinic carbons of the epoxy alcohol (CH=CH) (CH3) groups at 0.883. 13C NMR data (Fig. 2) indicated the
at 132.481 and 123.697, epoxide carbons (O–C–H) at 56.461 presence of olefinic carbons of the isomers (CH=CH) at
FIG. 2. 13C NMR spectrum of diol isomers. Chemical shifts (ppm): 132.739, 130.188, 129.154, and 125.118
(CH=CH), 71.349 carbon attached to the terminal hydroxyl group, 62.403 and 62.113 (C12 and C13),
37.150–22.424 (CH2)n, and 13.866 (CH3). See Figure 1 for abbreviation.
JAOCS, Vol. 77, no. 8 (2000)

LITHIUM ALUMINUM HYDRIDE REDUCTION OF VERNONIA OIL
877
FIG. 3. (A) Gas chromatogram of the isolated diols from the vernonia oil methyl esters/lithium aluminum hydride
(VOME/LAH) reaction in tetrahydrofuran (THF). Peak labeled as 1 is assigned to 12-hydroxy-cis-9-octadecenol, and
peak labeled as 2 is assigned to 13-hydroxy-cis-9-octadecenol. (B) Gas chromatogram of the acetylated mixture
from the VOME/LAH reaction in THF. Peaks labeled as 3, 4, 5, 6, 7, and 8 are due to the presence of the acetates of
palmityl alcohol, linoleyl alcohol, oleyl alcohol, stearyl alcohol, and diols respectively. (C) Gas chromatogram of
the spiked acetylated diols. Peak labeled as 7 is assigned to 12-hydroxy-cis-9-octadecenol (contribution from the
acetylated diol from the reduction of castor oil methyl ester), and peak labeled as 8 is assigned to 13-hydroxy-cis-9-
octadecenol.
132.739, 130.188, 129.154, and 125.118; carbon attached to duct mixture. The chromatogram (Fig. 3B) of the acetylated
the terminal hydroxyl group (C–OH) at 71.349; carbons C12 mixture also showed two peaks, labeled as 7 and 8, both of
and C13 attached to the internal hydroxyl groups of the iso- which represent higher retention times relative to the diols.
mers at 62.403 and 62.113; carbons of the methylene groups Other peaks in Figure 3B, labeled as 3, 4, 5, and 6 are due to
(CH2)n at 37.150–22.424; and carbons of methyl group (CH3) the presence of acetates of palmityl alcohol, linoleyl alcohol,
at 13.866. We should note that the complexity of the spectrum oleyl alcohol, and stearyl alcohol, respectively. The mass
in Figure 2 is another confirmation that the product was a spectra of the acetylated diols (MW 368), showed no diag-
mixture of diol isomers. A total of 30 carbons is indicated nostic ions that would enable unequivocal characterization.
(less than the expected 39), apparently due to the overlap of Both spectra exhibited the following major ions (m/z): at
equivalent chemical shifts.
308 (M – CH3CO2H), 248 (M – 2CH3CO2H), and 265
Acetylation of the diols. The GC of the isolated diols (Fig. (308 – CH3CO). Furthermore, an acetylated diol (12-hy-
3A) showed two peaks, labeled as 1 and 2. In order to further droxy-cis-9-octadecenol), which was obtained from the reac-
confirm the occurrence of the diols, we acetylated this pro- tion of castor oil with LAH in THF, was spiked with the
JAOCS, Vol. 77, no. 8 (2000)

878
E.B. ELHILO ET AL.
7. Walborsky, H.M., and C. Colombini, Reduction of Glycidic Es-
ters with Lithium Aluminum Hydride, J. Org. Chem. 27:
2387–2390 (1962).
8. Ernest, E.L., and D.W. Delmonte, The Mechanism of Halide Re-
ductions with Lithium Aluminum Hydride. Vl. Reduction of
Certain Bromohydrins and Epoxides, J. Am. Chem. Soc.
80:1744–1752 (1958).
9. Ernest, E.L., and M.N. Rerick, Reductions with Metal Hydride.
VII. Reduction of Epoxides with Lithium Aluminum Hydride-
Aluminum Chloride, Ibid. 82:1362–1367 (1960).
10. Ayorinde, F.O., B.D. Butler, and M.T. Clayton, Vernonia gala-
mensis: A Rich Source of Epoxy Acids, J. Am. Oil Chem. Soc.
67:844–845 (1990).
acetylated diols of VOME/LAH reaction in THF. The GC of
the spiked acetylated diols (Fig. 3C), showed an increase in
peak 7, which implied that 13-hydroxy-cis-9-octadecenol was
the major product of VOME/LAH reaction in THF. However,
an accurate isomeric ratio has not been determined at this
time.
ACKNOWLEDGMENT
This research was supported by the Howard University Fac-
ulty Research Support Grant Program: Mordecai W. Johnson
Award.
11. Fernandez, A.M., C.J. Murphy, M.T. Decosta, J.A. Mason, and
L.H. Sperling, in Polymer Applications of Renewable Resource
Materials, edited by C.E. Carraher, Jr., and L.H. Sperling,
Plenum Press, New York, 1983, pp. 273–288.
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[Received November 18, 1999; accepted June 27, 2000]
JAOCS, Vol. 77, no. 8 (2000)