バクセン酸
- 動物脂肪に含まれる炭素数18のcis-11-モノ不飽和脂肪酸
WordNet
- street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
- any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
- having the characteristics of an acid; "an acid reaction"
PrepTutorEJDIC
- 酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/10/02 18:00:29」(JST)
[Wiki en表示]
Vaccenic acid |
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IUPAC name
(E)-Octadec-11-enoic acid
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Identifiers |
CAS number |
693-72-1 Y |
PubChem |
5281127 |
ChemSpider |
4444571 Y |
ChEBI |
CHEBI:28727 Y |
Jmol-3D images |
Image 1 |
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CCCCCC/C=C/CCCCCCCCCC(O)=O
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InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7+ Y
Key: UWHZIFQPPBDJPM-BQYQJAHWSA-N Y
InChI=1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,9-17H2,1H3,(H,19,20)/b8-7+
Key: UWHZIFQPPBDJPM-BQYQJAHWBK
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Properties |
Molecular formula |
C18H34O2 |
Molar mass |
282.461 g/mol |
Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
Infobox references |
Vaccenic acid is an omega-7 fatty acid. It is a naturally occurring trans-fatty acid found in the fat of ruminants and in dairy products such as milk, butter, and yogurt.[1] It is also the predominant fatty acid comprising trans fat in human milk.[2][3]
Its IUPAC name is (E)-11-octadecenoic acid, and its lipid shorthand name is 18:1 trans-11. The name was derived from the Latin vacca (cow).[4]
Vaccenic acid was discovered in 1928 in animal fats and butter. It is the main trans fatty acid isomer present in milk fat.[4] Mammals convert it into rumenic acid, a conjugated linoleic acid,[5][6] where it shows anticarcinogenic properties.[7]
Its stereoisomer, cis-vaccenic acid, also an omega-7 fatty acid, is found in Sea Buckthorn (Hippophae rhamnoides) oil.[8] Its IUPAC name is (Z)-11-octadecenoic acid, and its lipid shorthand name is 18:1 cis-11.
Health[edit]
A 2008 study at the University of Alberta suggests that vaccenic acid feeding in rats over 16 weeks resulted in lowered total cholesterol, lowered LDL cholesterol and lower triglyceride levels. The researchers are preparing to conduct further research, including human clinical trials.[9]
Vaccenic acid is also found in human orbitofrontal cortex of patients with bipolar disorder and schizophrenia.[10][11]
Oxidation of omega-7 unsaturated fatty acids on the skin surface, such as palmitoleic acid and vaccenic acid, may be the cause of the phenomenon commonly known as old person smell.[12]
References[edit]
- ^ Natural trans fats may be good for you. May 19, 2008
- ^ Precht, D and J.Molkentin C18:1, C18:2, and C8:3 trans and cis fatty acid isomers including conjugated cis delta 9, trans delta 11 linoleic acid (CLA) as well as total fat composition of German human milk lipids, Nahrung 1999 43(4) 233-244
- ^ Friesen, R, and S.M. Innis, Trans Fatty acids in Human milk in Canada declined with the introduction of trans fat food labeling, J. Nut 2006, 136 2558-2561
- ^ a b F. Destaillats, E. Buyukpamukcu, P.-A. Golay, F. Dionisi and F. Giuffrida (2005). "Letter to the Editor: Vaccenic and Rumenic Acids, A Distinct Feature of Ruminant Fats". Journal of Dairy Science 88 (449): 449. doi:10.3168/jds.S0022-0302(05)72705-3.
- ^ Bauman, Dale. "cis-9, trans-11 CLA - A Potent Anticarcinogen Found in Milk Fat". Archived from the original on 2006-09-07. Retrieved 2007-01-15.
- ^ Banni S, Angioni E, Murru E, Carta G, Melis M, Bauman D, Dong Y, Ip C (2001). "Vaccenic acid feeding increases tissue levels of conjugated linoleic acid and suppresses development of premalignant lesions in rat mammary gland". Nutr Cancer 41 (1–2): 91–7. doi:10.1207/S15327914NC41-1&2_12. PMID 12094634.
- ^ Lock AL, Corl BA, Barbano DM, Bauman DE, Ip C. (October 1, 2004). "The anticarcinogenic effect of trans-11 18:1 is dependent on its conversion to cis-9, trans-11 CLA by delta9-desaturase in rats". J Nutr 134 (10): 2698–704. PMID 15465769. Retrieved 2007-01-15.
- ^ Federal Research Centre for Nutrition and Food - Institute for Lipid Research. "Seed Oil Fatty Acids Database".
- ^ AFNS. Alberta natural trans fat research earns global recognition. April 2, 2008.
- ^ McNamara, RK; Jandacek, R; Rider, T; Tso, P; Hahn, CG; Richtand, NM; Stanford, KE (2007). "Abnormalities in the fatty acid composition of the postmortem orbitofrontal cortex of schizophrenic patients: gender differences and partial normalization with antipsychotic medications". Schizophr Res 91 (1–3): 37–50. doi:10.1016/j.schres.2006.11.027. PMC 1853256. PMID 17236749.
- ^ McNamara, RK; Jandacek, R; Rider, T; Tso, P; Stanford, KE; Hahn, CG; Richtand, NM (2008). "Deficits in docosahexaenoic acid and associated elevations in the metabolism of arachidonic acid and saturated fatty acids in the postmortem orbitofrontal cortex of patients with bipolar disorder". Psychiatry Research 160 (3): 285–299. doi:10.1016/j.psychres.2007.08.021. PMC 2620106. PMID 18715653.
- ^ S. Haze, Y. Gozu, S. Nakamura, Y. Kohno, K. Sawano, H. Ohta and K. Yamazaki (2001). "2-Nonenal Newly Found in Human Body Odor Tends to Increase with Aging". Journal of Investigative Dermatology 116 (4): 520–524. doi:10.1046/j.0022-202x.2001.01287.x. PMID 11286617.
UpToDate Contents
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English Journal
- Effect of supplementing different oils: Linseed, sunflower and soybean, on animal performance, carcass characteristics, meat quality and fatty acid profile of veal from "Rubia Gallega" calves.
- González L, Moreno T, Bispo E, Dugan ME, Franco D.Author information Departamento de Producción Animal, Centro de Investigaciones Agrarias de Mabegondo (C.I.A.M), INGACAL, Apdo 10, 15080 A Coruña, Spain. Electronic address: gongonlaura@hotmail.com.AbstractThe fatty acid (FA) composition of longisimus dorsi (LD) and subcutaneous fat (SCF) from Rubia Gallega (RG) calves was compared for three dietary oil sources (linseed, LO; sunflower, SFO or soybean, SYO). Oils were added (4.5%) to a commercial concentrate and no differences on animal performance, carcass characteristics or meat quality among diets were noted. Total n-3 polyunsaturated FA (PUFA) increased in LD and SCF when feeding LO diet (P<0.001). The trans(t) FA profiles were dominated by t11-18:1, except when feeding SFO diet, where ∑t6- to t10-18:1 exceeded t11-18:1 leading the highest (∑t6-to t10-18:1)/t11-18:11 ratio in LD (P<0.05). The overall changes in n-3 PUFA and t18:1 when feeding LO and SYO could be viewed as positive for human health, but quantitatively it was apparent that most dietary PUFA were completely biohydrogenated. Inhibiting PUFA biohydrogenation will be an important next step to improve the FA composition of RG cattle.
- Meat science.Meat Sci.2014 Feb;96(2):829-36. doi: 10.1016/j.meatsci.2013.09.027. Epub 2013 Oct 10.
- The fatty acid (FA) composition of longisimus dorsi (LD) and subcutaneous fat (SCF) from Rubia Gallega (RG) calves was compared for three dietary oil sources (linseed, LO; sunflower, SFO or soybean, SYO). Oils were added (4.5%) to a commercial concentrate and no differences on animal performance, ca
- PMID 24200577
- Trans-vaccenate is Δ13-desaturated by FADS3 in rodents.
- Rioux V, Pédrono F, Blanchard H, Duby C, Boulier-Monthéan N, Bernard L, Beauchamp E, Catheline D, Legrand P.Author information Laboratoire de Biochimie-Nutrition Humaine, Agrocampus Ouest-Institut National de la Recherche Agronomique (INRA) USC2012, Rennes, France.AbstractFatty acid desaturases play critical roles in regulating the biosynthesis of unsaturated fatty acids in all biological kingdoms. As opposed to plants, mammals are so far characterized by the absence of desaturases introducing additional double bonds at the methyl-end site of fatty acids. However, the function of the mammalian fatty acid desaturase 3 (FADS3) gene remains unknown. This gene is located within the FADS cluster and presents a high nucleotide sequence homology with FADS1 (Δ5-desaturase) and FADS2 (Δ6-desaturase). Here, we show that rat FADS3 displays no common Δ5-, Δ6- or Δ9-desaturase activity but is able to catalyze the unexpected Δ13-desaturation of trans-vaccenate. Although there is no standard for complete conclusive identification, structural characterization strongly suggests that the Δ11,13-conjugated linoleic acid (CLA) produced by FADS3 from trans-vaccenate is the trans11,cis13-CLA isomer. In rat hepatocytes, knockdown of FADS3 expression specifically reduces trans-vaccenate Δ13-desaturation. Evidence is presented that FADS3 is the first "methyl-end" fatty acid desaturase functionally characterized in mammals.
- Journal of lipid research.J Lipid Res.2013 Dec;54(12):3438-52. doi: 10.1194/jlr.M042572. Epub 2013 Sep 25.
- Fatty acid desaturases play critical roles in regulating the biosynthesis of unsaturated fatty acids in all biological kingdoms. As opposed to plants, mammals are so far characterized by the absence of desaturases introducing additional double bonds at the methyl-end site of fatty acids. However, th
- PMID 24070791
- Adipose tissue trans-fatty acids and changes in body weight and waist circumference.
- Hansen CP, Berentzen TL, Ostergaard JN, Dahm CC, Hellgren LI, Schmidt EB, Tjønneland A, Sørensen TI, Overvad K, Jakobsen MU.Author information Section for Epidemiology, Department of Public Health, Aarhus University, Bartholins Allé 2, DK-8000 Aarhus C, Denmark.AbstractPrevious studies have suggested that the intake of trans-fatty acids (TFA) plays a role in the development of obesity. The proportions of adipose tissue fatty acids not synthesised endogenously in humans, such as TFA, usually correlate well with the dietary intake. Hence, the use of these biomarkers may provide a more accurate measure of habitual TFA intake than that obtained with dietary questionnaires. The objective of the present study was to investigate the associations between the proportions of specific TFA in adipose tissue and subsequent changes in weight and waist circumference (WC). The relative content of fatty acids in adipose tissue biopsies from a random sample of 996 men and women aged 50-64 years drawn from a Danish cohort study was determined by GC. Baseline data on weight, WC and potential confounders were available together with information on weight and WC 5 years after enrolment. The exposure measures were total trans-octadecenoic acids (18 : 1t), 18 : 1 Δ6-10t, vaccenic acid (18 : 1 Δ11t) and rumenic acid (18 : 2 Δ9c, 11t). Data were analysed using multiple regression with cubic spline modelling. The median proportion of total adipose tissue 18 : 1t was 1·52 % (90 % central range 0·98, 2·19) in men and 1·47 % (1·01, 2·19) in women. No significant associations were observed between the proportions of total 18 : 1t, 18 : 1 Δ6-10t, vaccenic acid or rumenic acid and changes in weight or WC. The present study suggests that the proportions of specific TFA in adipose tissue are not associated with subsequent changes in weight or WC within the exposure range observed in this population.
- The British journal of nutrition.Br J Nutr.2013 Nov 29:1-9. [Epub ahead of print]
- Previous studies have suggested that the intake of trans-fatty acids (TFA) plays a role in the development of obesity. The proportions of adipose tissue fatty acids not synthesised endogenously in humans, such as TFA, usually correlate well with the dietary intake. Hence, the use of these biomarkers
- PMID 24286469
Japanese Journal
- Altered Fatty Acid Profile in the Liver and Serum of Stroke-Prone Spontaneously Hypertensive Rats : Reduced Proportion of cis-Vaccenic Acid
- Tanaka Shizuyo,Kojiguchi Chiho,Yamazaki Tohru [他]
- Journal of Oleo Science 62(11), 933-948, 2013-11
- NAID 40019836655
- 松岡 寛樹,須永 晃多,宮下 さとみ [他],砂原 由佳里,深沢 聡美,下田 未歩,木村 紀久,高橋 仁恵,高橋 朝歌,平田 大介
- 日本食品科学工学会誌 60(3), 117-124, 2013
- Ames試験により塩蔵ダイコンのアセトニトリル抽出物中に抗変異原性を有する画分を見いだした.機器分析により,活性成分の一つとしてパルミチン酸を同定した.そこで,塩蔵ダイコンおよび市販タクアン漬け製品について,脂肪酸の定量解析を行った.主要な脂肪酸として,α-リノレン酸,リノール酸およびパルミチン酸が見いだされた.その他にパルミトレイン酸,ステアリン酸,オレイン酸および(<I>Z< …
- NAID 130003367982
- 北海道産ナガイモ凍結乾燥物の脂質の組成およびヒト結腸がん細胞増殖抑制作用
- 山崎 民子,荒井 克仁,松下 容子 [他],得字 圭彦,川原 美香,大庭 潔,木下 幹朗,大西 正男
- 日本食品科学工学会誌 : Nippon shokuhin kagaku kogaku kaishi = Journal of the Japanese Society for Food Science and Technology 58(12), 567-575, 2011-12-15
- ナガイモ根茎の脂溶性成分に神経細胞保護作用が報告されているが,ナガイモの脂質成分はこれまで未詳であった.今回,著者らは北海道十勝産ナガイモの凍結乾燥物を用いて脂質成分の化学的組成を調べるとともに,不ケン化物のヒト結腸がん細胞に対する作用を検討した.ナガイモの脂質成分は微量(0.4%)であったが,アシルグリセロール類と遊離脂肪酸の他に,2種の中性ステロール脂質(アシルステロールと遊離ステロール),5 …
- NAID 10030333422
Related Links
- Vaccenic acid Vaccenic acid IUPAC name (E)-Octadec-11-enoic acid Identifiers CAS number 5281127 SMILES CCCCCCC=CCCCCCCCCCC(=O)O Properties Molecular formula ... my.chemeurope.com With an accout for my ...
- Scientific Name CAS Registry No. 11-octadecenoic acid 506-17-2 Molecular Name Common Name C18 H34 O2 vaccenic acid Other Names 11(Z)-Octadecenoic acid; 11-cis-octadecenoic acid; 11-cis-vaccenic acid; cis-vaccenic acid
Related Pictures
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[★]
- 英
- vaccenic acid
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- 11-オクタデセン酸 11-octadecenoic acid