19356-22-0

Basic information

• Product Name: 13-hydroperoxylinolenic acid
• Synonyms: 13-hydroperoxylinolenic acid;LINOLENATEHYDROPEROXIDE;LINOLENICACIDHYDROPEROXIDE;(9Z,12Z,15Z)-9,12,15-Octadecatrieneperoxoic acid;α-Linorenic acid hydroperoxide
• CAS NO: 19356-22-0
• Molecular Formula: C₁₈H₃₀O₃
• Molecular Weight: 294.48
• Mol File: 19356-22-0.mol

Chemical Properties

• Boiling Point: 376.19°C (rough estimate)
• Flash Point: 137.2°C
• Appearance: /
• Density: 1.0726 (rough estimate)
• Vapor Pressure: 1.49E-08mmHg at 25°C
• Refractive Index: 1.5450 (estimate)
• CAS DataBase Reference: 13-hydroperoxylinolenic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 13-hydroperoxylinolenic acid(19356-22-0)
• EPA Substance Registry System: 13-hydroperoxylinolenic acid(19356-22-0)

Safety Data

• Hazardous Substances Data: 19356-22-0(Hazardous Substances Data)

Usage

Chemical structure

13-hydroperoxylinolenic acid is a fatty acid hydroperoxide derived from linolenic acid.

Biosynthesis

It is a key intermediate in the biosynthesis of jasmonic acid, a plant hormone involved in response to environmental stress and defense against pathogens.

Formation

13-hydroperoxylinolenic acid is formed through the oxidation of linolenic acid by lipoxygenases.

Reactions

It can undergo enzymatic or non-enzymatic reactions to produce jasmonic acid and other related signaling molecules.

Role in plant defense

13-hydroperoxylinolenic acid plays a pivotal role in regulating plant responses to various biotic and abiotic stresses, making it a crucial component in plant defense and adaptation mechanisms.

InChI:InChI=1/C18H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)21-20/h3-4,6-7,9-10,20H,2,5,8,11-17H2,1H3/b4-3-,7-6-,10-9-

Upstream product

• 90563-52-3 α-methylindole 
• 463-40-1 (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid 

Downstream Products

• 809-51-8 7-ketocholesteryl acetate 
• 1256-31-1 3β-acetoxy-5,6-epoxycholestane 
• 17974-77-5 cholest-5-ene-3β,7-diol 3-monoacetate 
• 84619-17-0 (9E,12E,15E)-Octadeca-9,12,15-trienoic acid (3S,8S,9S,10R,13R,14S,17R)-3-acetoxy-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-7-yl ester 
• 138809-17-3 (9Z,12Z)-(15,16-epoxy)octadeca-9,12-dienoic acid 

Related news

An enzymatic formation of 13-oxo-trideca-9,11-dienoic acid from 13-hydroperoxylinolenic acid (cas 19356-22-0) by a homolytic hydroperoxide lyase in elicitor-treated soybean cotyledons08/03/2019

An activity of homolytic hydroperoxide lyase (HPLS) catalyzing the specific cleavage of 13-hydroperoxylinolenic acid to form a volatile compound and 13-oxo acid was found in the enzyme extract from soybean cotyledons. 2-Penten-l-ol was characterized as a volatile metabolite by gas chromatography...detailed

Relevant articles and documents

UVA irradiation of fatty acids and their oxidized products substantially increases their ability to generate singlet oxygen

UVA radiation plays an important role for adverse reactions in human tissue. UVA penetrates epidermis and dermis of skin being absorbed by various biomolecules, especially endogenous photosensitizers. This may generate deleterious singlet oxygen (1O2) that oxidizes fatty acids in cell membranes, lipoproteins, and other lipid-containing structures such as the epidermal barrier. Indications exist that fatty acids are not only the target of 1O2 but also act as potential photosensitizers under UVA irradiation, if already oxidized. Five different fatty acids in ethanol solution (stearic, oleic, linoleic, linolenic and arachidonic acid) were exposed to UVA radiation (355 nm, 100 mW) for 30 seconds. 1O 2 luminescence was detected time-resolved at 1270 nm and confirmed in spectrally-resolved experiments. The more double bonds fatty acids have the more 1O2 photons were detected. In addition, fatty acids were continuously exposed to broadband UVA for up to 240 min. During that time span, UVA absorption and 1O2 luminescence substantially increased with irradiation time, reached a maximum and decreased again. HPLC-MS analysis showed that the amount of peroxidized fatty acids and the 1O2 generation increased and decreased in parallel. This indicates the high potential of peroxidized fatty acids to produce 1O2 under UVA irradiation. In conclusion, fatty acids along with peroxidized products are weak endogenous photosensitizers but become strong photosensitizers under continuous UVA irradiation. Since fatty acids and their oxidized products are ubiquitous in living cells and in skin, which is frequently and long-lasting exposed to UVA radiation, this photosensitizing effect may contribute to initiation of deleterious photooxidative processes in tissue.

N-(15,16-Dihydroxylinoleoyl)-glutamine and N-(15,16-epoxylinoleoyl)-glutamine isolated from oral secretions of lepidopteran larvae

N-(15,16-Dihydroxylinoleoyl)-glutamine (1) and N-(15,16-epoxylinoleoyl)-glutamine (2) and were identified in the regurgitant of lepidopteran larvae (Spodoptera exigua and Spodoptera frugiperda) by LC-MS. After methanolysis and derivatisation with MSTFA, the positions of the hydroxy groups of 1 were identified by GC-MS. The structures of both conjugates were confirmed by synthesis.