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γ-亚麻酸

不饱和脂肪酸
6篇引用文献 COA COA
有货

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货号 (SKU) 包装规格 是否现货 价格 数量
L111861-50mg
 50mg 现货 Stock Image
L111861-100mg
 100mg 现货 Stock Image
L111861-500mg
 500mg 现货 Stock Image
L111861-1g
 1g 现货 Stock Image
大包装询价 收藏夹 比较  SDS下载  DATASHEET  质量标准
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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 Moligand™, ≥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

γ-亚麻酸已被用作气相色谱法的分析标准品。 可用于有关体重增加的营养研究和可能的肿瘤抑制药物。γ-亚麻酸用于研究不饱和脂肪酸的氧化/过氧化机制和预防。

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.
纯度 ≥97%

关联靶点（人）

CASP6 Tchem 胱天蛋白酶-6(Caspase-6) (1 活性数据)
活性类型 活性值-log(M) 作用机制 期刊 参考文献(PubMed IDs)
F2 Tclin Thrombin (11687 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
ESR1 Tclin Estrogen receptor alpha (17718 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
PGR Tclin Progesterone receptor (8562 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
ADRA2A Tclin Alpha-2a adrenergic receptor (9450 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
AR Tclin Androgen Receptor (11781 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
VDR Tclin Vitamin D receptor (26531 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
GABRA1 Tclin GABA receptor alpha-1 subunit (399 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
MAOA Tclin Monoamine oxidase A (11911 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
DRD1 Tclin Dopamine D1 receptor (9720 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
ACHE Tclin Acetylcholinesterase (18204 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
PTGS1 Tclin Cyclooxygenase-1 (9233 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SLC6A2 Tclin Norepinephrine transporter (10102 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SRD5A2 Tclin Steroid 5-alpha-reductase 2 (937 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SLC6A4 Tclin Serotonin transporter (12625 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
ADRA1A Tclin Alpha-1a adrenergic receptor (8359 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
OPRM1 Tclin Mu opioid receptor (19785 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
DRD3 Tclin Dopamine D3 receptor (14368 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SLC6A3 Tclin Dopamine transporter (10535 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
PPARA Tclin Peroxisome proliferator-activated receptor alpha (9197 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
KCNH2 Tclin HERG (29587 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
PDE3A Tclin Phosphodiesterase 3A (3309 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
TBXA2R Tclin Thromboxane A2 receptor (5717 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
PDE4A Tclin Phosphodiesterase 4A (1943 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
ADORA3 Tchem Adenosine A3 receptor (15931 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
HRH3 Tclin Histamine H3 receptor (10389 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
KDR Tclin Vascular endothelial growth factor receptor 2 (20924 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
FASN Tchem Fatty acid synthase (3390 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
GLP1R Tclin Glucagon-like peptide 1 receptor (111429 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
CASP6 Tchem Caspase-6 (1213 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
HEK293 (82097 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
FFAR1 Tchem Free fatty acid receptor 1 (4763 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
POLK Tbio DNA polymerase kappa (8653 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
POLI Tchem DNA polymerase iota (116820 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
POLH Tchem DNA polymerase eta (21678 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
L3MBTL1 Tchem Lethal(3)malignant brain tumor-like protein 1 (14536 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
PMP22 Tbio Peripheral myelin protein 22 (699 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
CBX1 Tbio Chromobox protein homolog 1 (92434 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
RGS4 Tchem Regulator of G-protein signaling 4 (13867 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
F7 Tchem Coagulation factor VII/tissue factor (740 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
GLS Tchem Glutaminase kidney isoform, mitochondrial (16997 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID

关联靶点（其它种属）

ampC Beta-lactamase AmpC (62480 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Trypsin (394 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Ppard Peroxisome proliferator-activated receptor delta (358 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Hdac6 Histone deacetylase 6 (222 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Plasmodium falciparum (966862 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
GCN5 Histone acetyltransferase GCN5 (89 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
rep Replicase polyprotein 1ab (378 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
TGR Thioredoxin glutathione reductase (28579 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID
SARS-CoV-2 (38078 活性数据)
活性类型 Relation Activity value Units Action Type 期刊 PubMed Id doi Assay Aladdin ID

作用机制

作用机制 Action Type target ID Target Name Target Type Target Organism Binding Site Name 参考文献

名称和识别符

PubChem SID 488195218
分子类型 小分子
IIUPAC Name (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid
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
Smiles CCCCCC=CCC=CCC=CCCCCC(=O)O
Isomeric SMILES CCCCC/C=C\C/C=C\C/C=C\CCCCC(=O)O
分子量 278.43
Beilstein号 1712253
Reaxy-Rn 8151168
Reaxys-RN link address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=8151168&ln=

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
分子量 278.400 g/mol
XLogP3 5.900
氢键供体数Hydrogen Bond Donor Count 1
氢键受体数Hydrogen Bond Acceptor Count 2
可旋转键计数Rotatable Bond Count 13
精确质量Exact Mass 278.225 Da
单同位素质量Monoisotopic Mass 278.225 Da
拓扑极表面积Topological Polar Surface Area 37.300 Ų
重原子数Heavy Atom Count 20
形式电荷Formal Charge 0
复杂度Complexity 301.000
同位素原子数Isotope Atom Count 0
定义的原子立体中心计数Defined Atom Stereocenter Count 0
未定义的原子立体中心计数Undefined Atom Stereocenter Count 0
定义的键立体中心计数Defined Bond Stereocenter Count 3
未定义的键立体中心计数Undefined Bond Stereocenter Count 0
所有立体化学键的总数The total count of all stereochemical bonds 3
共价键合单元计数Covalently-Bonded Unit Count 1

安全和危险性（GHS）

象形图 GHS07
信号词 警告
危险声明

H315: 引起皮肤刺激

H319: 引起严重眼睛刺激

H335: 可能引起呼吸道刺激
预防措施声明

P261: 避免吸入灰尘/烟雾/气体/雾/蒸汽/喷雾

P264: 处理后要彻底洗手。

P271: 仅在室外或通风良好的地方使用。

P280: 戴防护手套/穿防护服/戴防护眼罩/戴防护面具。

P321: 特殊处理（请参阅此标签上的...）。

P302+P352: 如皮肤沾染：用水充分清洗。

P304+P340: 如误吸入：将人转移到空气新鲜处，保持呼吸舒适体位。

P305+P351+P338: 如进入眼睛：用水小心冲洗几分钟。如戴隐形眼镜并可方便地取出，取出隐形眼镜。继续冲洗。

P362+P364: 脱掉沾污的衣服，清洗后方可重新使用。

P405: 密闭存放

P403+P233: 存放在通风良好的地方。保持容器密闭。

P501: 将内容物/容器处理到。。。

P264+P265: 处理后彻底洗手[和…]。不要触摸眼睛。

P337+P317: 如果眼睛刺激持续：寻求医疗帮助。

P332+P317: 如果出现皮肤刺激：请寻求医疗帮助。

P319: 如果你感到不适，请寻求医疗帮助。
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

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批号(Lot Number) 证书类型 货号
G2514395 分析证书 L111861
G2514396 分析证书 L111861
G2514397 分析证书 L111861
D2511438 分析证书 L111861
D2511437 分析证书 L111861
D2511439 分析证书 L111861
F2405465 分析证书 L111861
F2405466 分析证书 L111861
F2405476 分析证书 L111861
D2407373 分析证书 L111861
H2328671 分析证书 L111861
H2328673 分析证书 L111861
H2328681 分析证书 L111861
F2312897 分析证书 L111861
F2312931 分析证书 L111861
D2324844 分析证书 L111861
D2324866 分析证书 L111861
D2324868 分析证书 L111861
D2324896 分析证书 L111861
D2324901 分析证书 L111861
F2221125 分析证书 L111861
F2221132 分析证书 L111861
F2221133 分析证书 L111861
J2227058 分析证书 L111861
K2214110 分析证书 L111861

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引用文献

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,  9  ((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,  7  ((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,  6  ((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]
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