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1 Frank David Research Institute for Chromatography President Kennedy Park B- Kortrijk, Belgium Pat Sandra University of Gent Krijgslaan 281 S4, B-9000 Gent Belgium Allen K. Vickers Agilent Technologies, Inc. 91 Blue Ravine Road Folsom, CA USA (FAME) cis-trans FAME 3 cis-trans (DB23) FAME cis-trans cistrans (FAME) ( ) () 1

2 1 C4:0 C:0 C12:0 C14:0 C16:0 C16:1 C18:0 cis-9- C18:1- cis (n9) trans-9- C18:1- trans (n9) cis-9,12- C18:2 - cis (n6) trans-9,12- C18:2 - trans (n6) cis-9,12,15- - C18:3 (n3) cis-6,9,12- - C18:3 (n6) C:0 cis-11- C:1 (n9) cis-11,14- C:2 (n6) cis-11,14,17- C:3 (n3) cis-8,11, C:3 (n6) cis-5,8,11,14- C:4 (n6) cis-5,8,11,14,17- EPA C:5 (n3) C22:0 cis-13- C22:1 (n9) cis-7,,13,16- C22:4 (n6) cis-4,7,,13,16,19- DHA C22:6 (n3) C24:0 cis-15- C24:1 (n9) () HP-FFAP [1] FAME ( ) (cis/trans) FAME 3 DB-Wax C4 () C24 ( ) FAME cis- trans- FAME FAME 1 1 2

3 FAME DB-23 cis- 5,8,11,14,17- (EPA C:5 3) cis-4,7,,13,16,19- (DHA C22:6 3) FAME -3 cis- trans- cis- trans- cis- trans- cis-trans trans- FAME cis- trans- 1 FAME 0.01% 0.1% (w/v) 37 (Supelco #18919) 0 mg C4 C24 FAME ( 2% 4%) ml FAME mg/ml [1-5] [5] ml ( ) 0 mg ml 2 N (0 ml 11.2 g) 0 µl 2 ml (FID) Agilent 6890 GC Agilent DB-Wax 3 DB-23 4 FAME Analysis DB-Wax DB-23 No cis-trans cis-trans Some overlap "Simple" mixtures Milk fat Complex mixtures cis-trans Partial cis-trans separation (EPA, Omega 3 DHA) analysis Fish oils Complex mixtures Excellent cis-trans cis-trans separation Olive oil Refined ( ) (hydrogenated) oils 1 (FAME) 3

4 2 1 (DB-Wax) Agilent 6890 GC / FID Agilent 5973 MSD Agilent 7683 (p/n ) m 0.25 mm 0.25 µm DB-Wax (J&W ) GC-FID 2 1 µl 1/ 53 kpa ( 36 cm/s) /min 2 3 /min 18 2 ml/min4 ml/min ml/min 3 2 (DB-23) Agilent 6890 GC / FID Agilent 5973 MSD Agilent 7683 (p/n ) m 0.25 mm 0.15 µm DB-23 (J&W ) GC-FID 2 1 µl 1/ 2 kpa ( 33 cm/s) /min 2 4 /min 5 2 ml/min4 ml/min ml/min 4 3A 3B () Agilent 6890 GC / FID Agilent 5973 MSD Agilent 7683 (p/n ) A 0 m 0.25 mm 0.2 µm (J&W A7) B m 0.25 mm 0.2 µm (J&W ) GC-FID 2 1 µl 1/ A B 2 ml/min A /min 2 5 /min 5 B /min ml/min4 ml/min ml/min 4

5 37 FAME DB-Wax 2 Norm. 0 C8:0 C12:0 90 C4:0 C:0 C16:0 C6:0 C14:0 C18:1 c+t DB-wax 70 C11:0 C13:0 C14:1 C15:0 C15:1 C18:0 C16:1 C17:0 C17:1 C18:2 c+t C18:3 n6 C18:3 n3 C:0 C:1 C:2 C: 3n6 + C21:0 C:3 n3 C:4 C:5 C22:0 C22:1 C22:2 C23:0 C24:0 C22:6 + C24: FAME GC-FID m 0.25 mm 0.25 µm DB-Wax 1 ( 2 ) min cis- trans- C18: min cis- trans- C18: min C:3 n6 C21:0.73 min C22:6 C24: min 3 (CRM 164 [6]) 5

6 Norm. 0 DB-wax C14:0 C16:0 C18:1 c+t 90 C18:0 70 C12:0 C4:0 C:0 C6:0 C8:0 C14:1 C15:0 C15:1 C16:1 C17:0 C18:2 c+t C18:3 n (CRM 164) GC-FID m 0.25 mm 0.25 µm DB-Wax 1 ( 2) m 0.25 mm 0.15 µm DB FAME 4 Norm C8:0 C:0 C12:0 C14:0 C16:0 DB C6:0 C18:0 C18:1, cis C4:0 C11:0 C13:0 C14:1 C15:0 C15:1 C16:1 C18:1, trans C17:0 C17:1 C18:2, trans C18:2, cis C18:3 n6 C18:3 n3 C:0 C:1n9 C21:0 C:2 C:3 n6 C:3 n3 C:4 n6 C22:0 C:5 C22:1 C22:2 C23:0 C24:0 C24:1 C22: FAME GC-FID m 0.25 mm 0.15 µm DB-23 2 ( 3) 6

7 cis/trans EPA (19.15 min) DHA (22.38 min) EPA DHA -3 5 EPA DHA Norm C12:0 C14:0 C14:1 C15:0 C15:1 C16:0 C16:1 C17:0 C17:1 C18:0 C18:1, trans C18:2, trans C18:1, cis C18:2, cis C18:3 n6 C18:3 n3 C:0 C:1n9 C21:0 C:2 C:3 n6 C:4 n6 C:3 n3 C22:0 C:5 (EPA) C22:1 C23:0 C22:2 DB-23 C24:0 C22:6 (DHA) C24: GC-FID m 0.25 mm 0.15 µm DB-23 2 ( 3)

8 Norm C4:0 C6:0 C8:0 C:0 C11:0 C12:0 C13:0 C14:0 C14:1 C15:0 C15:1 C16:0 C16:1 C17:0 C17:1 C18:0 C18:1 trans C18:1 cis C18:2 trans C18:2 cis C:0 C18:3 n6 C18:3 n3 C:1 C21:0 C:2 C2 + C :3 n6 C22:1 C:3 n3 C:4 C23:0 C22:2 C:5 C24:0 C24:1 C22: FAME GC-FID 0 m 0.25 mm 0.2 µm C22:0 C:3 (n-6) 24.7 min cis- trans- 5 C18:1 cis- trans- 7 Norm. 90 c6 c11 70 c9 18:1 t6 t C18:1 GC-FID 0 m 0.25 mm 0.2 µm 3A ( 4A) 8

9 4 C18:2 (trans-trans cis-trans trans-cis cis-cis) 8 Norm. C18:2 tt ct tc cc C18:2 GC-FID 0 m 0.25 mm 0.2 µm 3A ( DB-23 (cis-trans) DB C18: trans-c18:1(n9) cis-c18:1 (n9) 9 C18:1 9

10 pa 0 18:1 trans 18:2 DB-23 18: min pa 35 18:1 cis 25 18:0 18:1 trans C18:1 m 0.25 mm 0.15 µm DB-23 ( ) 0 m 0.25 mm 0.2 µm 1 cis-trans trans- trans- cis-

11 Norm trans-c18:1 2. trans-c18:2 3. trans-c18: FAME GC-FID 0 m 0.25 mm 0.2 µm 3A ( 4) trans- (C18:2 C18:3) EC Regulation 2568/91 [5]. 4 ( A- A) 0 m 35 (QC) m ( 4 - B) ( 4 B) 11 11

12 Norm C18:0 C18:1 C18:2 12 C16:0 11 C16:1 9 C18:3 8 7 C:0 C:1 6 C18:1 trans FAME GC-FID m 0.25 mm 0.2 µm 3B ( 4) EC regulation [5] FAME 3 1. DB-Wax cis-trans 2. DB-23 FAME EPA DHA 3 cis-trans 3. cis-trans (QC) 3. IUPAC, Standard methods for Analysis of Oils, Fats and Derivatives, Blackwell Scientific Publications, IUPAC Method International Standard ISO 154, version (ISO 154/02) (can be ordered from 5. EU regulation 2568/91, Official Journal EU, document L248, 5/9/ EC, Bureau of Reference (BCR), Brussels, Belgium (see catalog at Web 1. W. W. Christie, Gas Chromatography and Lipids, A Practical Guide, (1989), The Oily Press, Ayr, Scotland (ISBN O-X). 2. AOAC Official Methods of Analysis (00), method Ce Agilent Agilent Technologies, Inc. 05 Printed in Japan August, JAJP

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