为了获得访问"阿拉丁铁蛋"实时聊天框的流畅支持体验,建议您使用Chrome浏览器或选择360浏览器极速模式(如何切换极速模式?),感谢您选择我们!

γ-亚麻酸

不饱和脂肪酸
规格或纯度: 97%
有货

库存信息

关闭

库存信息

关闭

库存信息

关闭

库存信息

关闭
货号 (SKU) 包装规格 是否现货 价格 数量
L111861-50mg
50mg 期货 Stock Image
L111861-100mg
100mg 现货 Stock Image
L111861-500mg
500mg 现货 Stock Image
L111861-1g
1g 现货 Stock Image
查看相关系列
羧酸 羧酸封端剂

基本描述

别名 全顺式-6,9,12-十八碳三烯酸 | 顺,顺,顺-6,9,12-十八碳三烯酸
英文别名 (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid | gamma-Linolenic acid | (Z,Z,Z)-6,9,12-Octadecatrienoic acid
规格或纯度 97%
英文名称 γ-Linolenic acid
生化机理 不饱和脂肪酸。推定的抗癌剂。亚油酸衍生物。诱导产生ROS。使NFκB失活。也可能通过过氧化物酶体增殖物激活的受体(PPAR)刺激其磷酸化和易位
储存温度 -20°C储存,充氩
运输条件 超低温冰袋运输
备注 如果有可能,您尽量在使用的当天配置溶液,并在当天使用完它。但是,如果您需要预先配制储备溶液,我们建议您将溶液等份保存在-20°C的密封小瓶中。通常,它们最多可以使用一个月。在使用前和打开样品瓶之前,我们建议您让您的产品在室温下平衡至少1小时。需要更多关于溶解度,用法和处理的建议吗?请访问我们的常见问题(FAQ)页面以获取更多详细信息。
产品介绍

Usually used as an analytical standard in gas chromatography,and also used in nutritional studies regarding weight regain and as a possible tumor suppression agent. γ-linolenic acid is used in studies on the mechanisms and prevention of oxidation/peroxidation of unsaturated fatty acids.

Usually used as an analytical standard in gas chromatography,and also used in nutritional studies regarding weight regain and as a possible tumor suppression agent. γ-linolenic acid is used in studies on the mechanisms and prevention of oxidation/peroxidation of unsaturated fatty acids.

名称和标识符

PubChem SID 488195218
IUPAC Name (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
INCHI InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-
InChi Key VZCCETWTMQHEPK-QNEBEIHSSA-N
Canonical SMILES CCCCCC=CCC=CCC=CCCCCC(=O)O
Isomeric SMILES CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O
WGK Germany 3
PubChem CID 5280933
分子量 278.43
Beilstein号 1712253

化学和物理性质

密度 0.92
敏感性 对光、空气、热敏感
折光率 1.48
闪点(℉) 230.0 °F
闪点(℃) 110°C

安全和危险性(GHS)

象形图
ghs07

Harmful

信号词 Warning
危险声明 H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
预防措施声明 P261,P305+P351+P338,P280,P302+P352,P321,P405,P501,P264,P271,P304+P340,P403+P233,P362+P364,P264+P265,P337+P317,P332+P317,P319
WGK Germany 3
Merck Index 5507
个人防护装备 Eyeshields,full-face respirator (US),Gloves,multi-purpose combination respirator cartridge (US),type ABEK (EN14387) respirator filter

质检证书(COA)

质检报告(COA)

输入批号以搜索COA:

相关文档

质检报告COA

请输入批号:


产品问答

产品问答

登录提交问题 Hover me 请先登录再提交问题
您提交该产品问题后,我们会在1-2个工作日内给您答复,您可以登录"我的账号",然后点击"我的产品问答"查看答案

参考文献

1. D F Horrobin.  (1992-01-01)  The use of gamma-linolenic acid in diabetic neuropathy..  Agents and actions. Supplements,  37  ():  (120-144).  [PMID:1321553]
2. A Bordoni.  (1990-03-31)  [Significance and motivation of the clinical use of essential fatty acid derivatives, especially gamma-linolenic acid]..  La Clinica terapeutica,  132  ((6)):  (383-392).  [PMID:2158408]
3. V A Ziboh,C C Miller,Y Cho.  (2000-01-05)  Metabolism of polyunsaturated fatty acids by skin epidermal enzymes: generation of antiinflammatory and antiproliferative metabolites..  The American journal of clinical nutrition,  71  ((1 Suppl)):  (361S-366S).  [PMID:10617998]
4. Elizabeth C Leigh-Firbank,Anne M Minihane,David S Leake,John W Wright,Margaret C Murphy,Bruce A Griffin,Christine M Williams.  (2002-05-16)  Eicosapentaenoic acid and docosahexaenoic acid from fish oils: differential associations with lipid responses..  The British journal of nutrition,  87  ((5)):  (435-445).  [PMID:12010583]
5. Berthold Koletzko,Ulrike Sauerwald,Ursula Keicher,Helmut Saule,Susanne Wawatschek,Hansjosef Böhles,Karin Bervoets,Mathilde Fleith,Gayle Crozier-Willi.  (2003-10-22)  Fatty acid profiles, antioxidant status, and growth of preterm infants fed diets without or with long-chain polyunsaturated fatty acids. A randomized clinical trial..  European journal of nutrition,  42  ((5)):  (243-253).  [PMID:14569405]
6. .  (2004-03-10)  Gamma-linolenic acid (GLA). Monograph..  Alternative medicine review : a journal of clinical therapeutic,  ((1)):  (70-78).  [PMID:15005646]
7. Jim-Wen Liu,Stephen J DeMichele,John Palombo,Lu-Te Chuang,Christine Hastilow,Emil Bobik,Yung-Sheng Huang.  (2004-06-10)  Effect of long-term dietary supplementation of high-gamma-linolenic canola oil versus borage oil on growth, hematology, serum biochemistry, and N-6 fatty acid metabolism in rats..  Journal of agricultural and food chemistry,  52  ((12)):  (3960-3966).  [PMID:15186123]
8. Undurti N Das.  (2006-12-16)  Tumoricidal and anti-angiogenic actions of gamma-linolenic acid and its derivatives..  Current pharmaceutical biotechnology,  ((6)):  (457-466).  [PMID:17168663]
9. Marie A Schirmer,Stephen D Phinney.  (2007-05-22)  Gamma-linolenate reduces weight regain in formerly obese humans..  The Journal of nutrition,  137  ((6)):  (1430-1435).  [PMID:17513402]
10. Michael M Meguid,Michael J Glade,Frank A Middleton.  (2008-08-30)  Weight regain after Roux-en-Y: a significant 20% complication related to PYY..  Nutrition (Burbank, Los Angeles County, Calif.),  24  ((9)):  (832-842).  [PMID:18725080]
11. David S Wishart,Craig Knox,An Chi Guo,Roman Eisner,Nelson Young,Bijaya Gautam,David D Hau,Nick Psychogios,Edison Dong,Souhaila Bouatra,Rupasri Mandal,Igor Sinelnikov,Jianguo Xia,Leslie Jia,Joseph A Cruz,Emilia Lim,Constance A Sobsey,Savita Shrivastava,Paul Huang,Philip Liu,Lydia Fang,Jun Peng,Ryan Fradette,Dean Cheng,Dan Tzur,Melisa Clements,Avalyn Lewis,Andrea De Souza,Azaret Zuniga,Margot Dawe,Yeping Xiong,Derrick Clive,Russ Greiner,Alsu Nazyrova,Rustem Shaykhutdinov,Liang Li,Hans J Vogel,Ian Forsythe.  (2008-10-28)  HMDB: a knowledgebase for the human metabolome..  Nucleic acids research,  37  ((Database issue)):  (D603-D610).  [PMID:18953024]
12. Julianne Lindemann,E David Pampe,Joanna J Peterkin,Patti Orozco-Cronin,Gil Belofsky,Dean Stull.  (2009-10-09)  Clinical study of the effects on asthma-related QOL and asthma management of a medical food in adult asthma patients..  Current medical research and opinion,  25  ((12)):  (2865-2875).  [PMID:19811112]
13. Nikolaos Psychogios,David D Hau,Jun Peng,An Chi Guo,Rupasri Mandal,Souhaila Bouatra,Igor Sinelnikov,Ramanarayan Krishnamurthy,Roman Eisner,Bijaya Gautam,Nelson Young,Jianguo Xia,Craig Knox,Edison Dong,Paul Huang,Zsuzsanna Hollander,Theresa L Pedersen,Steven R Smith,Fiona Bamforth,Russ Greiner,Bruce McManus,John W Newman,Theodore Goodfriend,David S Wishart.  (2011-03-02)  The human serum metabolome..  PloS one,  ((2)):  (e16957-e16957).  [PMID:21359215]
14. Klemens König,Peter Rosenberger,Valbona Mirakaj.  (2012-01-12)  Supplementation in acute lung injury..  JAMA,  307  ((2)):  (145-145).  [PMID:22235080]
15. Patrick Tso,Jody Caldwell,Dana Lee,Gregory P Boivin,Stephen J DeMichele.  (2012-01-24)  Comparison of growth, serum biochemistries and n-6 fatty acid metabolism in rats fed diets supplemented with high-gamma-linolenic acid safflower oil or borage oil for 90 days..  Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association,  50  ((6)):  (1911-1919).  [PMID:22265940]
16. Fengyun Qin,Linzhi Kang,Liqiong Guo,Junfang Lin,Jingshen Song,Yinhua Zhao.  (2012-02-14)  Composition of transgenic soybean seeds with higher γ-linolenic acid content is equivalent to that of conventional control..  Journal of agricultural and food chemistry,  60  ((9)):  (2200-2204).  [PMID:22324875]
17. O Ya Lukivskaya,E Naruta,V Sadovnichy,S Kirko,V U Buko.  (2012-02-24)  Reversal of experimental ethanol-induced liver steatosis by borage oil..  Phytotherapy research : PTR,  26  ((11)):  (1626-1631).  [PMID:22359349]
18. C Vaquerizo Alonso,T Grau Carmona,M Juan Díaz.  (2012-03-21)  Guidelines for specialized nutritional and metabolic support in the critically-ill patient: update. Consensus SEMICYUC-SENPE: hyperglycemia and diabetes mellitus..  Nutricion hospitalaria,  26 Suppl 2  ():  (46-49).  [PMID:22411519]
19. Hector L Lopez.  (2012-06-01)  Nutritional interventions to prevent and treat osteoarthritis. Part I: focus on fatty acids and macronutrients..  PM & R : the journal of injury, function, and rehabilitation,  ((5 Suppl)):  (S145-S154).  [PMID:22632694]
20. Jie Fu,Xue-Wei Zhang,Kai Liu,Qing-Shan Li,Li-Rong Zhang,Xian-Hui Yang,Zhi-Ming Zhang,Chang-Zhu Li,Yin Luo,Zhen-Xiang He,Hai-Liang Zhu.  (2012-07-04)  Hypolipidemic activity in Sprague-Dawley rats and constituents of a novel natural vegetable oil from Cornus wilsoniana fruits..  Journal of food science,  77  ((8)):  (H160-H169).  [PMID:22747885]
21. Jutta Auberger,Stefan Vogt,Georg Hopfinger,Johannes Clausen,Richard Greil.  (2012-12-25)  Topical evening primrose oil for reduction of bortezomib-induced skin reactions..  Annals of hematology,  92  ((7)):  (995-996).  [PMID:23262668]
22. Brian R Jacobs,Vinay Nadkarni,Brahm Goldstein,Paul Checchia,Onsy Ayad,Judy Bean,Stephen DeMichele.  (2013-01-09)  Nutritional immunomodulation in critically ill children with acute lung injury: feasibility and impact on circulating biomarkers..  Pediatric critical care medicine : a journal of the Society of Critical Care Medicine and the World Federation of Pediatric Intensive and Critical Care Societies,  14  ((1)):  (e45-e56).  [PMID:23295853]
23. Inmaculada Tasset-Cuevas,Zahira Fernández-Bedmar,María Dolores Lozano-Baena,Juan Campos-Sánchez,Antonio de Haro-Bailón,Andrés Muñoz-Serrano,Angeles Alonso-Moraga.  (2013-03-06)  Protective effect of borage seed oil and gamma linolenic acid on DNA: in vivo and in vitro studies..  PloS one,  ((2)):  (e56986-e56986).  [PMID:23460824]
24. I S Mysiakina,Ia É Sergeeva,A A Ivashechkin,E P Feofilova.  (2013-04-25)  [Lipid composition of fungus Mucor hiemalis mycelium grown in the presence of trehalose, triacylglycerols, and itraconazole]..  Mikrobiologiia,  81  ((6)):  (726-732).  [PMID:23610922]
25. I S Mysiakina,Ia É Sergeeva,A A Ivashechkin,E P Feofilova.  (2013-04-25)  [Effect of biological factors on morphogenesis, growth, and lipid composition of fungus Mucor hiemalis mycelium]..  Mikrobiologiia,  81  ((6)):  (733-740).  [PMID:23610923]
26. Tiffany T Mayo,Farhan Khan,Christine Hunt,Kristy Fleming,Ramsey Markus.  (2013-08-01)  Comparative study on bruise reduction treatments after bruise induction using the pulsed dye laser..  Dermatologic surgery : official publication for American Society for Dermatologic Surgery [et al.],  39  ((10)):  (1459-1464).  [PMID:23899131]
27. Milan Gautam,Atsushi Izawa,Yuji Shiba,Hirohiko Motoki,Takahiro Takeuchi,Ayako Okada,Takeshi Tomita,Yusuke Miyashita,Jun Koyama,Uichi Ikeda.  (2014-09-06)  Importance of fatty acid compositions in patients with peripheral arterial disease..  PloS one,  ((9)):  (e107003-e107003).  [PMID:25191963]
28. Minho Kim,JaeGoo Kim,Yu-Kyong Shin,Ki-Young Kim.  (2020-03-27)  Gentisic Acid Stimulates Keratinocyte Proliferation through ERK1/2 Phosphorylation..  International journal of medical sciences,  17  ((5)):  (626-631).  [PMID:32210712]
29. D F Horrobin.  (1993-01-01)  The effects of gamma-linolenic acid on breast pain and diabetic neuropathy: possible non-eicosanoid mechanisms..  Prostaglandins, leukotrienes, and essential fatty acids,  48  ((1)):  (101-104).  [PMID:8380930]
30. J Hindo,C Hauville,S Rémita,P Thérond,M Couturier,D Jore,M Gardès-Albert.  (2000-01-12)  Evidence of the formation of different hydroperoxides in irradiated gamma-linolenate solutions: effect of micelle formation..  Radiation research,  153  ((2)):  (201-207).  [PMID:10629620]
31. Undurti N Das.  (2007-06-30)  Gamma-linolenic acid therapy of human glioma-a review of in vitro, in vivo, and clinical studies..  Medical science monitor : international medical journal of experimental and clinical research,  13  ((7)):  (RA119-RA131).  [PMID:17599036]
32. Tomáš Řezanka,Jaromír Lukavský,Lucie Siristova,Karel Sigler.  (2012-03-27)  Regioisomer separation and identification of triacylglycerols containing vaccenic and oleic acids, and α- and γ-linolenic acids, in thermophilic cyanobacteria Mastigocladus laminosus and Tolypothrix sp..  Phytochemistry,  78  ():  (147-155).  [PMID:22445652]
33. Ola M Omran.  (2012-05-12)  Histopathological study of evening primrose oil effects on experimental diabetic neuropathy..  Ultrastructural pathology,  36  ((4)):  (222-227).  [PMID:22574767]
34. Ulrike Mütze,Skadi Beblo,Linda Kortz,Claudia Matthies,Berthold Koletzko,Mathias Bruegel,Carmen Rohde,Joachim Thiery,Wieland Kiess,Uta Ceglarek.  (2012-08-23)  Metabolomics of dietary fatty acid restriction in patients with phenylketonuria..  PloS one,  ((8)):  (e43021-e43021).  [PMID:22912778]
35. Selvaraj Jubie,Palanisamy Dhanabal,Mohammed Afzal Azam,Nithyanantham Muruganantham,Rajagopal Kalirajan,Kannan Elango.  (2013-03-30)  Synthesis and characterization of some novel fatty acid analogues: a preliminary investigation on their activity against human lung carcinoma cell line..  Lipids in health and disease,  12  ():  (45-45).  [PMID:23537396]
36. Zosia Kmietowicz.  (2013-05-01)  Evening primrose oil and borage oil do not help eczema symptoms, finds Cochrane review..  BMJ (Clinical research ed.),  346  ():  (f2712-f2712).  [PMID:23628953]
37. Xiaofei Bai,Leng-Jie Huang,Sheng-Wen Chen,Benjamin Nebenfuehr,Brian Wysolmerski,Jui-Ching Wu,Sara K Olson,Andy Golden,Chao-Wen Wang.  (2020-08-21)  Loss of the seipin gene perturbs eggshell formation in Caenorhabditis elegans..  Development (Cambridge, England),  147  ((20)):  ().  [PMID:32820022]