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γ-亚麻酸甲酯

γ-亚麻酸甲酯用途

γ-亚麻酸甲酯(methyl GLA)是γ-亚麻油酸(GLA)的酯化版本,是ω-6脂肪酸,用作黑色素瘤细胞增殖抑制剂。γ-亚麻酸甲酯抑制ADP诱导的血小板聚集并诱导细胞凋亡[1][2][3][4][5]。

γ-亚麻酸甲酯名称

[ CAS 号 ]:
16326-32-2

[ 中文名 ]:
γ-亚麻酸甲酯

[ 英文名 ]:
Methyl γ-linolenate

[中文别名 ]:

[英文别名 ]:

γ-LINOLENIC ACID METHYL ESTER
Methyl (6Z,9Z,12Z)-6,9,12-octadecatrienoate
Methyl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate
MFCD00010455
Methyl g-linolenate

γ-亚麻酸甲酯生物活性

[ 描述 ]:

[ 相关类别 ]:

信号通路 >> 细胞凋亡 >> 细胞凋亡

研究领域 >> 癌症

[体外研究]

γ-亚麻酸甲酯(1-4μg/mL；72小时)诱导体外A-549肺癌细胞凋亡。然而,GLA是由于其在基因/癌基因水平上的作用,并通过改变BCl-2表达[1]。细胞凋亡分析[1]细胞系：A-549肺癌细胞系浓度：1、2、3和4μg/mL培养时间：72小时；在24小时、48小时和72小时观察结果：显示了细胞毒性,这可能是由于仅在肿瘤细胞中而非正常细胞中通过增加自由基生成来诱导肿瘤细胞凋亡。

[体内研究]

γ-亚麻酸甲酯可降低肝脏甘油三酯,并有EtOH诱导的脂肪肝的组织学证据[2]。γ-亚麻酸甲酯可显著降低正常和高脂血症大鼠血浆总胆固醇(TC)、甘油三酯(TG)、低密度脂蛋白胆固醇(LDL-C)、MDA、动脉粥样硬化指数(AI)和肝脏TC、MDA水平,并增加高密度脂蛋白胆甾醇(HDL-C)水平[3]。动物模型：EtOH诱导的肝病理大鼠模型(雄性Sprague-Dawley大鼠,250-300 g)[2]剂量：90 mL,50-60 mL给药：腹膜内注射；每天一次；结果：与盐水(40.2 mg/g)或橄榄油(42.8 mg/g)治疗相比,肝甘油三酯降低25.6 mg/g。高脂血症大鼠的肝脏指数(肝脏重量与体重之比)降低,但正常大鼠无明显影响。

[参考文献]

[1]. Jubie S, et al. Isolation of methyl gamma linolenate from Spirulina platensis using flash chromatography and its apoptosis inducing effect. BMC Complement Altern Med. 2015 Aug 4;15:263.

[2]. Segarnick DJ, et al. Gamma-linolenic acid inhibits the development of the ethanol-induced fatty liver. Prostaglandins Leukot Med. 1985 Mar;17(3):277-82.

[3]. Xiuqin K, et al. Studies on the hypolipidemic effects of gamma-linolenic acid methyl ester derived from Spirulina maxima[J]. Zhongguo hai Yang yao wu= Chinese Journal of Marine Drugs, 2003, 22(6): 30-34.

[4]. Williams, et al. Antithrombosis agent containing γ-linolenic acid or a functional derivative of it: Federal Republic of Germany, DE2749492[P]. 1978-05-11.

[5]. Hiyamuta, et al. Melanoma cell proliferation inhibitors containing γ-linolenic acid or its derivatives: Japan, JP2014141427[P]. 2014-08-07.

γ-亚麻酸甲酯物理化学性质

[ 密度 ]:
0.9±0.1 g/cm3

[ 沸点 ]:
385.4±0.0 °C at 760 mmHg

[ 分子式 ]:
C₁₉H₃₂O₂

[ 分子量 ]:
292.456

[ 闪点 ]:
101.5±23.2 °C

[ 精确质量 ]:
292.240234

[ PSA ]:
26.30000

[ LogP ]:
7.03

[ 外观性状 ]:
Liquid

[ 蒸汽压 ]:
0.0±0.8 mmHg at 25°C

[ 折射率 ]:
1.476

[ 储存条件 ]:
−20°C

γ-亚麻酸甲酯MSDS

详细MSDS(安全技术说明书)

γ-亚麻酸甲酯安全信息

[ 符号 ]:

GHS02, GHS07

[ 信号词 ]:
Danger

[ 危害声明 ]:
H225-H319

[ 警示性声明 ]:
P210-P280-P305 + P351 + P338-P337 + P313-P403 + P235

[ 个人防护装备 ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ 危害码 (欧洲) ]:
F

[ 风险声明 (欧洲) ]:
11

[ 安全声明 (欧洲) ]:
16

[ 危险品运输编码 ]:
UN 1993 / PGIII

[ WGK德国 ]:
3

[ 海关编码 ]:
2916190090

γ-亚麻酸甲酯合成路线

详细合成路线

γ-亚麻酸甲酯上下游产品

γ-亚麻酸甲酯上游产品

γ-亚麻酸甲酯下游产品

γ-亚麻酸甲酯海关

[ 海关编码 ]: 2916190090

[ 中文概述 ]:
2916190090 其他不饱和无环一元羧酸（包括其酸酐、酰卤化物，过氧化物和过氧酸以及它们的衍生物）。监管条件:AB(入境货物通关单,出境货物通关单)。增值税率:17.0%。退税率:9.0%。最惠国关税:6.5%。普通关税:30.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 丙烯酸、丙烯酸盐或酯应报明包装

[ 监管条件 ]: A.入境货物通关单 B.出境货物通关单

[ 检验检疫 ]: R.进口食品卫生监督检验 S.出口食品卫生监督检验 M.进口商品检验 N.出口商品检验

[ Summary ]:
2916190090 unsaturated acyclic monocarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives。supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward)。VAT:17.0%。tax rebate rate:9.0%。MFN tariff:6.5%。general tariff:30.0%

γ-亚麻酸甲酯文献

Weight regain after Roux-en-Y: a significant 20% complication related to PYY.

Nutrition 24 , 832-842, (2008)

Roux-en-Y gastric bypass (RYGB) produces rapid and dramatic weight loss in very heavy obese patients. Up to 20% cannot sustain their weight loss beyond 2 to 3 y after surgery.To identify putative etio...

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.

J. Agric. Food Chem. 52 , 3960-3966, (2004)

Dietary supplementation of a high-gamma-linolenic acid canola oil (HGCO) containing approximately 36% (w/w) of gamma-linolenic acid (GLA, 18:3n-6) from the seeds of a genetically transformed canola st...

Gamma-linolenate reduces weight regain in formerly obese humans.

J. Nutr. 137 , 1430-1435, (2007)

The purpose of this study was to determine whether gamma-linolenate (GLA) supplementation would suppress weight regain following major weight loss. Fifty formerly obese humans were randomized into a d...

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