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Catalogue Number
BD-D1368
Analysis Method
HPLC,NMR,MS
Specification
98%(HPLC)
Storage
-20℃
Molecular Weight
278.43
Appearance
colorless liquid
Botanical Source
Flaxseed
Structure Type
Aliphatics
Category
Standards;Natural Pytochemical;API
SMILES
CCC=CCC=CCC=CCCCCCCCC(=O)O
Synonyms
(9Z,12Z,15Z)-linolenic acid/9,12,15-all-cis-Octadecatrienoic acid/9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)-/Linolein,2-mono/2-linoleoyl-sn-glycerol/2-Monolinolein/(9Z,12Z,15Z)-Octadeca-9,12,15-trienoic acid/2-Glyceryl 9,12-octadecadienoate/9,12-Octadecadienoic acid (Z,Z)-,2-hydroxy-1-(hydroxymethyl)ethyl ester/linoleic acid monoacylglycerol/9,12,15-OCTADECATRIENOIC ACID, (Z,Z,Z)-/Glyceryl 2-linoleate/9Z,12Z,15Z-octadecatrienic acid/2-monolinoleoylglycerol/9Z,12Z,15Z-Octadecatrienoic acid/(9Z,12Z,15Z)-9,12,15-Octadecatrienoic acid/a-Linolenic Acid/octadecatrienoic acid/9,12,15-octadecatrienoic acid/alpha-linolenic acid/(all-Z)-9,12,15-Octadecatrienoic acid/(9Z,12Z)-1,3-dihydroxypropan-2-yl octadeca-9,12-dienoate/Linolenic acid/C18:3 (9,12,15-cis all)/2-Linoleoylglycerol/9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)- (9CI)
IUPAC Name
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
Applications
Density
0.9±0.1 g/cm3
Solubility
Methanol; Acetontrile
Flash Point
275.7±14.4 °C
Boiling Point
443.4±0.0 °C at 760 mmHg
Melting Point
InChl
InChl Key
WGK Germany
RID/ADR
HS Code Reference
2916150000
Personal Projective Equipment
Correct Usage
For Reference Standard and R&D, Not for Human Use Directly.
Meta Tag
provides coniferyl ferulate(CAS#:463-40-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate
No Technical Documents Available For This Product.
30379219
Objectives: Dietary omega-3 fatty acids have been efficacious in decreasing serum cholesterol levels and reducing the risk of cardiovascular disease. However, the metabolic and molecular changes induced by the omega-3 fatty acid α-linolenic acid (ALA), which is found in linseed oil, are not fully understood. In this study, we showed a correlation between ALA and insulin resistance, inflammation and endoplasmic reticulum stress (ERS).
Methods: We studied 40 male mice (C57/BL6) divided into 4 groups: a control (C) group, a control + omega-3/ALA (CA) group, a high-fat diet (HFD) (H) group and a high-fat diet + omega-3/ALA (HA) group. For 8 weeks, the animals in the H and HA groups were fed a high-fat (60%) diet, while the animals in the C and CA groups received regular chow. The diets of the CA and HA groups were supplemented with 10% lyophilized ALA.
Results: ALA supplementation improved glucose tolerance and reduced insulin resistance, as measured by intraperitoneal glucose tolerance tests and the homeostasis model assessment for insulin resistance, respectively. In addition, ALA reduced hepatic steatosis and modified the standard fat concentration in the liver of animals fed an HFD. Dietary ALA supplementation reduced the serum levels of interleukin 6 (IL-6), interleukin 1 beta (IL-1β) and monocyte chemoattractant protein-1 (MCP-1), increased the expression of important chaperones such as binding immunoglobulin protein (BIP) and heat shock protein 70 (HSP70) and reduced the expression of C/EBP-homologous protein (CHOP) and X-box binding protein 1 (XBP1) in hepatic tissues, suggesting an ERS adaptation in response to ALA supplementation.
Conclusions: Dietary ALA supplementation is effective in preventing hepatic steatosis; is associated with a reduction in insulin resistance, inflammation and ERS; and represents an alternative for improving liver function and obtaining metabolic benefits.
α-Linolenic Acid Prevents Hepatic Steatosis and Improves Glucose Tolerance in Mice Fed a High-Fat Diet
Natalia Bonissi Goncalves 1 , Rafael Ferraz Bannitz 1 , Bruna Ramos Silva 1 , Danielle Duran Becari 1 , Carolina Poloni 1 , Patricia Moreira Gomes 1 , Milton Cesar Foss 1 , Maria Cristina Foss-Freitas 1
2018 Oct 29
28818464
Oxidation products of the poly-unsaturated fatty acids (PUFAs) arachidonic acid, α-linolenic acid and docosahexaenoic acid are bioactive in plants and animals as shown for the cyclopentenones prostaglandin 15d-PGJ2 and PGA2, cis-(+)-12-oxophytodienoic acid (12-OPDA), and 14-A-4 neuroprostane. In this study an inexpensive and simple enzymatic multi-step one-pot synthesis is presented for 12-OPDA, which is derived from α-linolenic acid, and the analogous docosahexaenoic acid (DHA)-derived cyclopentenone [(4Z,7Z,10Z)-12-[[-(1S,5S)-4-oxo-5-(2Z)-pent-2-en-1yl]-cyclopent-2-en-1yl] dodeca-4,7,10-trienoic acid, OCPD]. The three enzymes utilized in this multi-step cascade were crude soybean lipoxygenase or a recombinant lipoxygenase, allene oxide synthase and allene oxide cyclase from Arabidopsis thaliana. The DHA-derived 12-OPDA analog OCPD is predicted to have medicinal potential and signaling properties in planta. With OCPD in hand, it is shown that this compound interacts with chloroplast cyclophilin 20-3 and can be metabolized by 12-oxophytodienoic acid reductase (OPR3) which is an enzyme relevant for substrate bioactivity modulation in planta.
One-pot Synthesis of Bioactive Cyclopentenones From α-Linolenic Acid and Docosahexaenoic Acid
Daniel Maynard 1 , Sara Mareike Muller 1 , Monika Hahmeier 1 , Jana Lowe 2 , Ivo Feussner 3 , Harald Groger 2 , Andrea Viehhauser 1 , Karl-Josef Dietz 4
2018 Apr 1
29926330
Harmful algal blooms (HABs) induced by Prorocentrum donghaiense occur frequently and cause a serious threat to the marine ecosystem. In this study, antialgal effects of α-linolenic acid (ALA) that is generally extracted from diverse macroalga on P. donghaiense were investigated. Specifically, the growth, cellular morphology and ultrastructure, reactive oxygen species (ROS) content, mitochondrial membrane potential (MMP), cytochrome C (Cyt-C), and caspase-9,3 activity of untreated and treated P. donghaiense were investigated. The results showed that ALA significantly inhibited the growth of P. donghaiense. Under ALA exposure, the cellular morphology and ultrastructure were damaged. ALA also induced ROS overproduction in the algal cells, decreased MMP, induced Cyt-C release, and activated caspase-9,3, which strongly relates to algal apoptosis. In summary, this study revealed the responses of morphology and physiology of P. donghaiense when exposed under ALA, and shows the potential of biotechnology on controlling P. donghaiense.
Antialgal effect; Apoptosis; Prorocentrum donghaiense; α-linolenic acid (ALA).
Antialgal Effects of α-Linolenic Acid on Harmful Bloom-Forming Prorocentrum Donghaiense and the Antialgal Mechanisms
Renjun Wang 1 , Jialin Chen 2 , Ning Ding 2 , Meiaoxue Han 2 , Jianguo Wang 2 , Pan Zhang 3 , Xiuxia Liu 2 , Ningning Zheng 2 , Peike Gao 4
2018 Sep
