Identification of acylglycerols containing dihydroxy fatty acids in castor oil by mass spectrometry

Jiann Tsyh Lin, Arthur J. Arcinas, Leslie A. Harden

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Ricinoleate, a monohydroxy fatty acid, in castor oil has many industrial uses. Dihydroxy fatty acids can also be used in industry. The C18 HPLC fractions of castor oil were analyzed by electrospray ionization mass spectrometry of lithium adducts to identify the acylglycerols containing dihydroxy fatty acids and the dihydroxy fatty acids. Four diacylglycerols identified were diOH18:1-diOH18:1, diOH18:2-OH18:1, diOH18:1-OH18:1 and diOH18:0-OH18:1. Eight triacylglycerols identified were diOH18:1-diOH18:1- diOH18:1, diOH18:1-diOH18:1-diOH18:0, diOH18:2-diOH18:1-OH18:1, diOH18:1-diOH18:1-OH18:1, diOH18:1-diOH18:0-OH18:1, diOH18:2-OH18:1-OH18:1, diOH18:1-OH18:1-OH18:1 and diOH18:0-OH18:1-OH18:1. The locations of fatty acids on the glycerol backbone were not determined. The structures of these three newly identified dihydroxy fatty acids were proposed as 11,12-dihydroxy-9- octadecenoic acid, 11,12-dihydroxy-9,13-octadecadienoic acid and 11,12-dihydroxyoctadecanoic acid. These individual acylglycerols were at the levels of about 0.5% or less in castor oil and can be isolated from castor oil or overproduced in a transgenic oil seed plant for future industrial uses.

Original languageEnglish (US)
Pages (from-to)359-365
Number of pages7
JournalLipids
Volume44
Issue number4
DOIs
StatePublished - Apr 2009
Externally publishedYes

Fingerprint

Castor Oil
Glycerides
Mass spectrometry
Mass Spectrometry
Fatty Acids
Oilseeds
Electrospray ionization
Plant Oils
Electrospray Ionization Mass Spectrometry
Diglycerides
Oleic Acid
Lithium
Glycerol
Seeds
Industry
Triglycerides
High Pressure Liquid Chromatography
Acids

Keywords

  • 11,12-Dihydroxy-9,13-octadecadienoic acid
  • 11,12-Dihydroxy-9-octadecenoic acid
  • 11,12-Dihydroxyoctadecanoic acid
  • Castor oil
  • Diacylglycerols
  • Dihydroxy fatty acids
  • Mass spectrometry
  • Ricinus communis L.
  • Triacylglycerols

ASJC Scopus subject areas

  • Biochemistry
  • Cell Biology
  • Organic Chemistry

Cite this

Identification of acylglycerols containing dihydroxy fatty acids in castor oil by mass spectrometry. / Lin, Jiann Tsyh; Arcinas, Arthur J.; Harden, Leslie A.

In: Lipids, Vol. 44, No. 4, 04.2009, p. 359-365.

Research output: Contribution to journalArticle

@article{2892ffbf63854b8284a3b633ca61084e,
title = "Identification of acylglycerols containing dihydroxy fatty acids in castor oil by mass spectrometry",
abstract = "Ricinoleate, a monohydroxy fatty acid, in castor oil has many industrial uses. Dihydroxy fatty acids can also be used in industry. The C18 HPLC fractions of castor oil were analyzed by electrospray ionization mass spectrometry of lithium adducts to identify the acylglycerols containing dihydroxy fatty acids and the dihydroxy fatty acids. Four diacylglycerols identified were diOH18:1-diOH18:1, diOH18:2-OH18:1, diOH18:1-OH18:1 and diOH18:0-OH18:1. Eight triacylglycerols identified were diOH18:1-diOH18:1- diOH18:1, diOH18:1-diOH18:1-diOH18:0, diOH18:2-diOH18:1-OH18:1, diOH18:1-diOH18:1-OH18:1, diOH18:1-diOH18:0-OH18:1, diOH18:2-OH18:1-OH18:1, diOH18:1-OH18:1-OH18:1 and diOH18:0-OH18:1-OH18:1. The locations of fatty acids on the glycerol backbone were not determined. The structures of these three newly identified dihydroxy fatty acids were proposed as 11,12-dihydroxy-9- octadecenoic acid, 11,12-dihydroxy-9,13-octadecadienoic acid and 11,12-dihydroxyoctadecanoic acid. These individual acylglycerols were at the levels of about 0.5{\%} or less in castor oil and can be isolated from castor oil or overproduced in a transgenic oil seed plant for future industrial uses.",
keywords = "11,12-Dihydroxy-9,13-octadecadienoic acid, 11,12-Dihydroxy-9-octadecenoic acid, 11,12-Dihydroxyoctadecanoic acid, Castor oil, Diacylglycerols, Dihydroxy fatty acids, Mass spectrometry, Ricinus communis L., Triacylglycerols",
author = "Lin, {Jiann Tsyh} and Arcinas, {Arthur J.} and Harden, {Leslie A.}",
year = "2009",
month = "4",
doi = "10.1007/s11745-008-3270-6",
language = "English (US)",
volume = "44",
pages = "359--365",
journal = "Lipids",
issn = "0024-4201",
publisher = "Springer Verlag",
number = "4",

}

TY - JOUR

T1 - Identification of acylglycerols containing dihydroxy fatty acids in castor oil by mass spectrometry

AU - Lin, Jiann Tsyh

AU - Arcinas, Arthur J.

AU - Harden, Leslie A.

PY - 2009/4

Y1 - 2009/4

N2 - Ricinoleate, a monohydroxy fatty acid, in castor oil has many industrial uses. Dihydroxy fatty acids can also be used in industry. The C18 HPLC fractions of castor oil were analyzed by electrospray ionization mass spectrometry of lithium adducts to identify the acylglycerols containing dihydroxy fatty acids and the dihydroxy fatty acids. Four diacylglycerols identified were diOH18:1-diOH18:1, diOH18:2-OH18:1, diOH18:1-OH18:1 and diOH18:0-OH18:1. Eight triacylglycerols identified were diOH18:1-diOH18:1- diOH18:1, diOH18:1-diOH18:1-diOH18:0, diOH18:2-diOH18:1-OH18:1, diOH18:1-diOH18:1-OH18:1, diOH18:1-diOH18:0-OH18:1, diOH18:2-OH18:1-OH18:1, diOH18:1-OH18:1-OH18:1 and diOH18:0-OH18:1-OH18:1. The locations of fatty acids on the glycerol backbone were not determined. The structures of these three newly identified dihydroxy fatty acids were proposed as 11,12-dihydroxy-9- octadecenoic acid, 11,12-dihydroxy-9,13-octadecadienoic acid and 11,12-dihydroxyoctadecanoic acid. These individual acylglycerols were at the levels of about 0.5% or less in castor oil and can be isolated from castor oil or overproduced in a transgenic oil seed plant for future industrial uses.

AB - Ricinoleate, a monohydroxy fatty acid, in castor oil has many industrial uses. Dihydroxy fatty acids can also be used in industry. The C18 HPLC fractions of castor oil were analyzed by electrospray ionization mass spectrometry of lithium adducts to identify the acylglycerols containing dihydroxy fatty acids and the dihydroxy fatty acids. Four diacylglycerols identified were diOH18:1-diOH18:1, diOH18:2-OH18:1, diOH18:1-OH18:1 and diOH18:0-OH18:1. Eight triacylglycerols identified were diOH18:1-diOH18:1- diOH18:1, diOH18:1-diOH18:1-diOH18:0, diOH18:2-diOH18:1-OH18:1, diOH18:1-diOH18:1-OH18:1, diOH18:1-diOH18:0-OH18:1, diOH18:2-OH18:1-OH18:1, diOH18:1-OH18:1-OH18:1 and diOH18:0-OH18:1-OH18:1. The locations of fatty acids on the glycerol backbone were not determined. The structures of these three newly identified dihydroxy fatty acids were proposed as 11,12-dihydroxy-9- octadecenoic acid, 11,12-dihydroxy-9,13-octadecadienoic acid and 11,12-dihydroxyoctadecanoic acid. These individual acylglycerols were at the levels of about 0.5% or less in castor oil and can be isolated from castor oil or overproduced in a transgenic oil seed plant for future industrial uses.

KW - 11,12-Dihydroxy-9,13-octadecadienoic acid

KW - 11,12-Dihydroxy-9-octadecenoic acid

KW - 11,12-Dihydroxyoctadecanoic acid

KW - Castor oil

KW - Diacylglycerols

KW - Dihydroxy fatty acids

KW - Mass spectrometry

KW - Ricinus communis L.

KW - Triacylglycerols

UR - http://www.scopus.com/inward/record.url?scp=63349104989&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=63349104989&partnerID=8YFLogxK

U2 - 10.1007/s11745-008-3270-6

DO - 10.1007/s11745-008-3270-6

M3 - Article

C2 - 19048323

AN - SCOPUS:63349104989

VL - 44

SP - 359

EP - 365

JO - Lipids

JF - Lipids

SN - 0024-4201

IS - 4

ER -