Shipping to Germany We Offer Worldwide Shipping
Login Wishlist

α-Linolenic acid

$120

  • Brand : BIOFRON

  • Catalogue Number : AV-P11858

  • Specification : 98%

  • CAS number : 463-40-1

  • Formula : C18H30O2

  • Molecular Weight : 278.43

  • PUBCHEM ID : 5280934

  • Volume : 0.2ml

Available on backorder

Quantity
Checkout Bulk Order?

Catalogue Number

AV-P11858

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

278.43

Appearance

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

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.

PMID

30379219

Abstract
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.
Title

α-Linolenic Acid Prevents Hepatic Steatosis and Improves Glucose Tolerance in Mice Fed a High-Fat Diet

Author

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

Publish date

2018 Oct 29

PMID

28818464

Abstract
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.
Title

One-pot Synthesis of Bioactive Cyclopentenones From α-Linolenic Acid and Docosahexaenoic Acid

Author

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

Publish date

2018 Apr 1

PMID

29926330

Abstract
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.
KEYWORDS

Antialgal effect; Apoptosis; Prorocentrum donghaiense; α-linolenic acid (ALA).

Title

Antialgal Effects of α-Linolenic Acid on Harmful Bloom-Forming Prorocentrum Donghaiense and the Antialgal Mechanisms

Author

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

Publish date

2018 Sep