Info: Read More
  • Home
  • Natural Products
  • Bioactive
  • Screening Libraries
  • Hot Products
  • Plant Catalog
  • Customer Support
  • Product Use Citation
  • About Us
  • Contact Us
  • How to Order
  • Delivery time
  • Science | Nature | Cell | View More
    Natural Products
    13(S)-Hydroxyoctadeca-9(Z),11(E)-dienoic acid (13-HODE)
    13(S)-Hydroxyoctadeca-9(Z),11(E)-dienoic acid (13-HODE)
    Information
    CAS No. 18104-45-5 Price $318 / 10mg
    Catalog No.CFN95307Purity>=98%
    Molecular Weight296.5Type of CompoundLipids
    FormulaC18H32O3Physical DescriptionOil
    Download     COA    MSDSSimilar structuralComparison (Web)  (SDF)
    Citing Use of our Products
    How to Order
    Orders via your E-mail:

    1. Product number / Name / CAS No.
    2. Delivery address
    3. Ordering/billing address
    4. Contact information
    Sent to Email: info@chemfaces.com
    Contact Us
    Order & Inquiry & Tech Support

    Tel: (0086)-27-84237683
    Fax: (0086)-27-84254680
    E-mail: manager@chemfaces.com
    Address: No. 83, CheCheng Rd., WETDZ, Wuhan, Hubei 430056, PRC
    Delivery time
    Delivery & Payment method

    1. Usually delivery time: Next day delivery by 9:00 a.m. Order now

    2. We accept: Wire transfer & Credit card & Paypal & Western Union
    * Packaging according to customer requirements(5mg, 10mg, 20mg and more). We shipped via FedEx, DHL, UPS, EMS and others courier.
    According to end customer requirements, ChemFaces provide solvent format. This solvent format of product intended use: Signaling Inhibitors, Biological activities or Pharmacological activities.
    Size /Price /Stock 10 mM * 1 mL in DMSO / $144.7 / In-stock
    Other Packaging *Packaging according to customer requirements(100uL/well, 200uL/well and more), and Container use Storage Tube With Screw Cap
    Our products had been exported to the following research institutions and universities, And still growing.
  • Lund University (Sweden)
  • University of Fribourg (Switzerland)
  • University of Toulouse (France)
  • Institute of Chinese Materia Me... (China)
  • University of Medicine and Phar... (Romania)
  • Centrum Menselijke Erfelijkheid (Belgium)
  • University of South Australia (Australia)
  • University of the Basque Country (Spain)
  • Chulalongkorn University (Thailand)
  • Kamphaengphet Rajabhat University (Thailand)
  • S.N.D.T. Women's University (India)
  • More...
  • Package
    Featured Products
    3-O-Caffeoylquinic acid methyl ester

    Catalog No: CFN92573
    CAS No: 123483-19-2
    Price: $198/10mg
    Ginsenoside F4

    Catalog No: CFN90757
    CAS No: 181225-33-2
    Price: $/mg
    Isochamaejasmine

    Catalog No: CFN92150
    CAS No: 93859-63-3
    Price: $418/5mg
    Ayanin

    Catalog No: CFN96157
    CAS No: 572-32-7
    Price: $/mg
    Viscidulin III

    Catalog No: CFN97488
    CAS No: 92519-91-0
    Price: $318/5mg
    Pinoresinol diglucoside

    Catalog No: CFN99994
    CAS No: 63902-38-5
    Price: $100/20mg
    Leachianone A

    Catalog No: CFN97560
    CAS No: 97938-31-3
    Price: $218/5mg

    13(S)-Hydroxyoctadeca-9(Z),11(E)-dienoic acid (13-HODE)

    13(S)-Hydroxyoctadeca-9(Z),11(E)-dienoic acid (13-HODE)
    Product Name 13(S)-Hydroxyoctadeca-9(Z),11(E)-dienoic acid (13-HODE)
    CAS No.: 18104-45-5
    Catalog No.: CFN95307
    Molecular Formula: C18H32O3
    Molecular Weight: 296.5 g/mol
    Purity: >=98%
    Type of Compound: Lipids
    Physical Desc.: Oil
    Source: The herbs of Piper cubeba
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Price: $318 / 10mg
    Inquire / Order: manager@chemfaces.com
    Technical Inquiries: service@chemfaces.com
    Tel: +86-27-84237783
    Fax: +86-27-84254680

    Address:
    1 Building, No. 83, CheCheng Rd., Wuhan Economic and Technological Development Zone, Wuhan, Hubei 430056, PRC
  • Biochem Pharmacol.2020, 178:114083
  • J Insect Sci.2020, 20(5):18.
  • Front Microbiol.2020, 11:583594.
  • Bio-protocol2018, 9(14):e3301
  • Pak J Pharm Sci.2019, 32(6)
  • Biomedicines.2020, 8(11):486.
  • JABS2020, 14:2(2020)
  • Plant J.2021, 107(6):1711-1723.
  • Braz J Med Biol Res. 2016, 49(7)
  • Plant Sci.2020, 301:110656.
  • Related Screening Libraries
    Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
    10 mM * 1 mL in DMSO / Inquiry / In-stock
    Related Libraries
  • Anticancer Compound Library
  • Anti-inflammatory Compound Library
  • Biological Activity
    Description: Anti-inflammatory.
    13-HODE down-regulates the thrombogenecity of the injured vessel wall surface.
    13-HODE prevents cell adhesion to endothelial cells and can inhibit cancer metastasis.
    In vitro:
    Free Radic Biol Med . 2019 Apr;134:598-603
    13-HODE, 9-HODE and ALOX15 as potential players in Rett syndrome OxInflammation[Pubmed: 30743046]
    Mutations in the MECP2 gene are the main cause of Rett syndrome (RTT), a pervasive neurodevelopmental disorder, that shows also multisystem disturbances associated with a metabolic component. The aim of this study was to investigate whether an increased production of oxidized linoleic acid metabolites, specifically 9- and 13-hydroxyoctadecadienoic acids (HODEs), can contribute to the altered the redox and immune homeostasis, suggested to be involved in RTT. Serum levels of 9- and 13-HODEs were elevated in RTT and associated with the expression of arachidonate 15-Lipoxygenase (ALOX15) in peripheral blood mononuclear cells (PBMCs). Omega-3 polyunsaturated fatty acids supplementation has shown to lower HODEs levels in RTT. Statistically significant correlation was demonstrated between the increased plasma HODEs levels and the lipoprotein-associated phospholipase A2 (Lp-PLA2) activity. Collectively, these findings reinforce the concept of the key role played by lipid peroxidation in RTT, and the possible ability of omega-3 polyunsaturated fatty acids supplementation in improving the oxinflammation status in RTT.
    Wien Klin Wochenschr . 1991;103(14):416-21.
    13-Hydroxyoctadecadienoic acid (13-HODE) metabolism and endothelial cell adhesion molecule expression: effect on platelet vessel wall adhesion[Pubmed: 1718092]
    Endothelial cells synthesize two important fatty acid metabolites, PGI2, which is synthesized from arachidonic acid via the cyclooxygenase pathway, and 13-HODE, which is synthesized from linoleic acid via the lipoxygenase pathway. PGI2 is synthesized following cell activation or injury while 13-HODE is synthesized in the unstimulated cell. While the role of PGI2 in platelet vessel wall interactions has been studied extensively, the role of 13-HODE in platelet vessel wall interactions is just now being understood. The present evidence suggests that 13-HODE is continuously synthesized in "resting" vessel wall cells and is in close juxtaposition with the ubiquous integrin adhesion molecule, the vitronectin receptor. The observation that the endothelial cell is not adhesive when 13-HODE and the vitronectin receptor are in close association and becomes adhesive when these two moieties dissociate and the vitronectin receptor relocates on the surface of the cell, provides further evidence that 13-HODE may induce conformational changes in the vitronectin receptor to reduce its ability to recognize its adhesive ligands. The additional observations that 13-HODE levels in both human and animal vessel walls are inversely related with vessel wall adhesivity, and that this adhesivity can be altered by altering 13-HODE synthesis, provides evidence that 13-HODE down-regulates the thrombogenecity of the injured vessel wall surface.
    Adv Exp Med Biol . 1997;433:291-4.
    The importance of linoleic acid metabolites in cancer metastasis and in the synthesis and actions of 13-HODE[Pubmed: 9561154]
    Large scale human epidemiological studies indicate that high intakes of linoleic acid protect against the development of cancer. One mechanism may be the generation of 13-HODE from linoleic acid. 13-HODE prevents cell adhesion to endothelial cells and can inhibit cancer metastasis. 13-HODE synthesis is enhanced by cyclic AMP. Gamma-linolenic acid, a desaturated metabolite of linoleic acid, causes substantial stimulation of 13-HODE synthesis. A fall in gamma-linolenic acid synthesis with age may be related to the age-related fall in 13-HODE formation.
    Cancer Epidemiol Biomarkers Prev . 1996 Jan;5(1):53-6.
    Decreased levels of 13-hydroxyoctadecadienoic acid (13-HODE) dehydrogenase in neoplastic tissue of human colon biopsies[Pubmed: 8770467]
    Recent studies have identified a role for the oxidation product of linoleic acid, 13-hydroxyoctadecadienoic acid (13-HODE) in cell proliferation. The enzyme 13-HODE dehydrogenase catalyzes the conversion of 13-HODE to 13-oxooctadecadienoic acid. This enzyme has been shown to correlate with the degree of differentiation of intestinal cells in both in vitro and in vivo models. Higher enzyme levels are found in more differentiated cell types. The present study was done to determine if enzyme levels of 13-HODE dehydrogenase are predictive of the differentiation status of biopsies from human colonic mucosa. Twenty-eight patients who underwent diagnostic colonoscopy (10 patients with adenocarcinoma and 18 with adenomatous polyps) had biopsies taken from both normal rectal mucosa and neoplastic mucosa. The determination of 13-HODE dehydrogenase activity was conducted by high-performance liquid chromatography analysis of all biopsy samples. Sixteen of the 18 patients with polyps had lower 13-HODE dehydrogenase activity in the adenoma than in the uninvolved rectal mucosa (P = 0.001). The colon adenocarcinomas also had less 13-HODE dehydrogenase activity in the cancer biopsy tissue than in uninvolved rectal mucosa (P = 0.041) These data are consistent with a role for 13-HODE dehydrogenase in intestinal cell differentiation. Understanding the precise role of this enzymatic reaction could be important potentially in the therapy and biology of colon cancer. In addition, measurements of 13-HODE dehydrogenase may be a useful parameter by which to ascertain the differentiation status of intestinal cells in vitro.
    13(S)-Hydroxyoctadeca-9(Z),11(E)-dienoic acid (13-HODE) Description
    Source: The herbs of Piper cubeba
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

    After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
    ChemFaces New Products and Compounds
    6-Hydroxywogonin

    Catalog No: CFN95009
    CAS No: 76844-70-7
    Price: $368/5mg
    10-O-trans-p-Feruloylscandoside

    Catalog No: CFN95392
    CAS No: 1428268-72-7
    Price: $318/10mg
    Methyl lucidente G

    Catalog No: CFN95058
    CAS No: 102607-20-5
    Price: $413/5mg
    Rosmarinyl glucoside

    Catalog No: CFN95297
    CAS No: 910028-78-3
    Price: $413/5mg
    Parishin G

    Catalog No: CFN95324
    CAS No: 952283-93-1
    Price: $318/10mg
    Isoeuphorbetin

    Catalog No: CFN95207
    CAS No: 50677-55-9
    Price: $318/5mg
    6'-Feruloylnodakenin

    Catalog No: CFN95202
    CAS No: 131623-14-8
    Price: $318/10mg
    Tessaric acid

    Catalog No: CFN95182
    CAS No: 58142-10-2
    Price: $318/5mg
    Recently, ChemFaces products have been cited in many studies from excellent and top scientific journals

    Cell. 2018 Jan 11;172(1-2):249-261.e12.
    doi: 10.1016/j.cell.2017.12.019.
    IF=36.216(2019)

    PMID: 29328914

    Cell Metab. 2020 Mar 3;31(3):534-548.e5.
    doi: 10.1016/j.cmet.2020.01.002.
    IF=22.415(2019)

    PMID: 32004475

    Mol Cell. 2017 Nov 16;68(4):673-685.e6.
    doi: 10.1016/j.molcel.2017.10.022.
    IF=14.548(2019)

    PMID: 29149595

    ACS Nano. 2018 Apr 24;12(4): 3385-3396.
    doi: 10.1021/acsnano.7b08969.
    IF=13.903(2019)

    PMID: 29553709

    Nature Plants. 2016 Dec 22;3: 16206.
    doi: 10.1038/nplants.2016.205.
    IF=13.297(2019)

    PMID: 28005066

    Sci Adv. 2018 Oct 24;4(10): eaat6994.
    doi: 10.1126/sciadv.aat6994.
    IF=12.804(2019)

    PMID: 30417089
    Calculate Dilution Ratios(Only for Reference)
    1 mg 5 mg 10 mg 20 mg 25 mg
    1 mM 3.3727 mL 16.8634 mL 33.7268 mL 67.4536 mL 84.317 mL
    5 mM 0.6745 mL 3.3727 mL 6.7454 mL 13.4907 mL 16.8634 mL
    10 mM 0.3373 mL 1.6863 mL 3.3727 mL 6.7454 mL 8.4317 mL
    50 mM 0.0675 mL 0.3373 mL 0.6745 mL 1.3491 mL 1.6863 mL
    100 mM 0.0337 mL 0.1686 mL 0.3373 mL 0.6745 mL 0.8432 mL
    * Note: If you are in the process of experiment, it's need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    Protocol
    Animal Research:
    Biochim Biophys Acta Mol Cell Biol Lipids . 2021 Mar;1866(3):158870.
    Linoleic acid-derived 13-hydroxyoctadecadienoic acid is absorbed and incorporated into rat tissues[Pubmed: 33340768]
    Linoleic acid (LNA)-derived 13-hydroxyoctadecadienoic acid (13-HODE) is a bioactive lipid mediator that regulates multiple signaling processes in vivo. 13-HODE is also produced when LNA is oxidized during food processing. However, the absorption and incorporation kinetics of dietary 13-HODE into tissues is not known. The present study measured unesterified d4-13-HODE plasma bioavailability and incorporation into rat liver, adipose, heart and brain following gavage or intravenous (IV) injection (n = 3 per group). Mass spectrometry analysis revealed that d4-13-HODE was absorbed within 20 min of gavage, and continued to incorporate into plasma esterified lipid fractions throughout the 90 min monitoring period (incorporation half-life of 71 min). Following IV injection, unesterified d4-13-HODE was rapidly eliminated from plasma with a half-life of 1 min. Analysis of tracer incorporation kinetics into rat tissues following IV injection or gavage revealed that the esterified tracer preferentially incorporated into liver, adipose and heart compared to unesterified d4-13-HODE. No tracer was detected in the brain. This study demonstrates that dietary 13-HODE is absorbed, and incorporated into peripheral tissues from esterified plasma lipid pools. Understanding the chronic effects of dietary 13-HODE exposure on peripheral tissue physiology and metabolism merits future investigation.
    Structure Identification:
    Lipids volume 28, pages325–330 (1993)
    Conversion of 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid to the corresponding hydroxy fatty acid by KOH: A kinetic study[Reference: WebLink]
    Transformation of 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid (13S-HPOD) to 13(S)-hydroxy-9(Z),11(E)-octadecadienoic acid (13S-HOD) under alkaline conditions (0.05 to 5 M KOH) occurred first-order with respect to 13S-HPOD concentration. Overall yield was about 80%. The energy of activation at higher concentrations (3.75 to 5 M KOH) was determined to be in the range of 15.3 to 15.6 kcal. Compared to the 13S-HPOD conversion, 13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid (13S-HPOT) was converted at a faster rate to the corresponding hydroxy fatty acid (13S-HOT), with the reaction also being first-order. Chiral phase high-performance liquid chromatography demonstrated that in the transformation the stereochemistry of both the 13S-HPOD and 13S-HPOT reactants was preserved. Manometric analyses of the KOH/13S-HPOD reaction showed an uptake of gas, which amounted to 11% of the mols of reactant 13S-HPOD on the assumption that the gas was O2. As there is a theoretical loss of 1 oxygen atom in the reaction, the fate of this oxygen (possiblyvia active oxygen species) may involve reaction with 13S-HPOD/13SHOD to form the 20% by-products.
    3-O-Caffeoylquinic acid methyl ester

    Catalog No: CFN92573
    CAS No: 123483-19-2
    Price: $198/10mg
    Ginsenoside F4

    Catalog No: CFN90757
    CAS No: 181225-33-2
    Price: $/mg
    Isochamaejasmine

    Catalog No: CFN92150
    CAS No: 93859-63-3
    Price: $418/5mg
    Ayanin

    Catalog No: CFN96157
    CAS No: 572-32-7
    Price: $/mg
    Viscidulin III

    Catalog No: CFN97488
    CAS No: 92519-91-0
    Price: $318/5mg
    Pinoresinol diglucoside

    Catalog No: CFN99994
    CAS No: 63902-38-5
    Price: $100/20mg
    Leachianone A

    Catalog No: CFN97560
    CAS No: 97938-31-3
    Price: $218/5mg