(±)8(9) ee 14(z) e

(±)14(15)-EE-8(Z)-E is a potent vasodilator in bovine coronary arteries. The synthesis of this analog involves the formation of the epoxide at the 14,15-double bond, however, epoxidation can also occur at the 8,9-double bond. (±)8(9)-EE-14(Z)-E is a minor product from the synthesis of (±)14(15)-EE-8(Z)-E. This compound has not been reported in the literature, and its biological activity is not known. It may serve as a tool to verify that the parent compound, (±)14(15)-EE-8(Z)-E, is pure and does not contain the 8,9-epoxy regioisomer.

GW406108X(Z/E) is a mixture of different configurations of GW406108X, which is an inhibitor of Kinesin-12 and ULK1 .

(E/Z)-Squalene ((E/Z)-AddaVax) regulates intracellular reactive oxidant species (ROS) production and induces apoptosis and necrosis in a concentration and time-dependent manner. (E/Z)-Squalene accumulates in the liver and lowers hepatic cholesterol and triglycerides.

(Z)-8-Dodecenyl acetate (Orfralure) is a pear psyllid sex pheromone, which can be used to study pear psyllid control.

TLR7/8/9 antagonist 2 is an orally active and highly bioavailable vTLR7/8/9 antagonist. TLR7/8/9 antagonist 2 inhibits HEK/hTLR7, HEK/hTLR8 and HEK/hTLR9 with IC50s of 0.011 μM, 0.029 μM and 0,052 μM, respectively. TLR7/8/9 antagonist 2 can be used to study auto-inflammatory diseases such as systemic lupus erythematosus or lupus nephritis.

(E/Z)-Sivopixant ((E/Z)-S-600918)is a potent P2X3 receptor antagonist, IC50 = 4 nM. (E/Z)-Sivopixant can be used for respiratory diseases research.

(E/Z)-Necrosulfonamide is a novel inhibitor of MLKL.

(E/Z)-4-Hydroxytamoxifen (Afimoxifene) is the active metabolite of tamoxifen and a selective estrogen receptor (ER) modulator that is widely used in the therapeutic and chemopreventive treatment of breast cancer.

(3ξ,4ξ,5ξ,6ξ,7ξ,11ξ)-3,6-Dihydroxy-8-oxo-9-eremophilene-12-oic acid, a phytotoxin recently identified in Alternaria alternata ssp. tenuissima isolates, is associated with fruit spots on apples.

7,10-dihydroxy-8(E)-Octadecenoic acid is a hydroxy fatty acid and metabolite of oleic acid that is produced byP. aeruginosafrom vegetable oils.1It is active against the food-borne pathogenic bacteriaS. aureus,S. typhimurium,L. monocytogenes,B. subtilis, andE. coli(MIC50s = 31.3, 125, 125, 62.5, and 250 μg/ml, respectively), as well as the plant pathogenic bacteriaErwinia,R. solanacearum,C. glutamicum, andP. syringae(MIC90s = 125, 125, 250, and 500 μg/ml, respectively).2,1 1.Sohn, H.-R., Bae, J.-H., Hou, C.T., et al.Antibacterial activity of a 7,10-dihydroxy-8(E)-octadecenoic acid against plant pathogenic bacteriaEnzyme Microb. Technol.53(3)152-153(2013) 2.Chen, K.Y., Kim, I.H., Hou, C.T., et al.Monoacylglycerol of 7,10-dihydroxy-8(E)-octadecenoic acid enhances antibacterial activities against food-borne bacteriaJ. Agric. Food Chem.67(29)8191-8196(2019)

9(Z),11(E)-Conjugated linoleic acid is an isomer of linoleic acid that has been found in beef and milk fat.1It binds to peroxisome proliferator-activated receptor α (PPARα; IC50= 140 nM) and activates the receptor in a reporter assay using COS-1 cells expressing mouse PPARα when used at a concentration of 100 μM.29(Z),11(E)-Conjugated linoleic acid inhibits TNF-α-inducedGLUT4expression and increases insulin-stimulated glucose transport in 3T3-L1 adipocytes.3Dietary administration of 9(Z)11(E)-conjugated linoleic acid reduces serum fasting glucose, insulin, and triglyceride levels and decreases white adipose tissue macrophage infiltration inob/obmice. It also increases body weight gain and body fat in weanling mice.4[Matreya, LLC. Catalog No. 1278] 1.Shultz, T.D., Chew, B.P., Seaman, W.R., et al.Inhibitory effect of conjugated dienoic derivatives of linoleic acid and β-carotene on the in vitro growth of human cancer cellsCancer Lett.63(2)125-133(1992) 2.Moya-Camarena, S.Y., Heuvel, J.P.V., Blanchard, S.G., et al.Conjugated linoleic acid is a potent naturally occurring ligand and activator of PPARαJ. Lipid Res.40(8)1426-1433(1999) 3.Moloney, F., Toomey, S., Noone, E., et al.Antidiabetic effects of cis-9, trans-11-conjugated linoleic acid may be mediated via anti-inflammatory effects in white adipose tissueDiabetes56(3)574-582(2007) 4.Pariza, M.W., Park, Y., and Cook, M.E.The biologically active isomers of conjugated linoleic acidProg. Lipid Res.40(4)283-298(2001)

(E,Z)-2-propyl-2-Pentenoic acid is a bioactive metabolite of valproic acid that exhibits the same profile and potency of anticonvulsant activity in animal models as its parent compound without any observed teratogenicity and hepatotoxicity.

11(Z),14(Z),17(Z)-Eicosatrienoic acid, an unsaturated fatty acid, supports the sustained replication of functional mitochondria in Saccharomyces cerevisiae (KD115) [1].

Compound 4, 14-Benzoylmesaconine-8-palmitate, is a lipo-alkaloid that can be isolated from A. toxicum [1].

15,16-Epoxy-12R-hydroxylabda-8(17),13(16),14-triene is a natural product for research related to life sciences. The catalog number is TN2631 and the CAS number is 61597-55-5.

Eicosapentaenoic acid is converted to epoxyeicosatetraenoic acids (EpETEs) by several cytochrome P450 isoforms. The major product of this epoxygenase pathway, (±)17(18)-EpETE , relaxes vascular and airway smooth muscle by activating large conductance Ca2+-activated K+ (BKCa) channels by directly interacting with BKα channel subunits. (±)8(9)-EpETE is an epoxygenase pathway product produced from EPA by CYP450 both in vitro and in vivo. The biological actions and physiological effects of this epoxide remain to be determined.

8-Epidiosbulbin E acetate exhibits broad-spectrum plasmid-curing activity against multidrug-resistant (MDR) bacteria, including vancomycin-resistant enterococci.

8-Epicrepiside E is a natural product of Saussurea, Asteraceae. The catalog number is TN3275 and the CAS number is 93395-30-3. 8-Epicrepiside E can be used as a reference standard.

(E/Z)-ZINC09659342 is an inhibitor of Lbc-Rho A interaction.

Docosapentaenoic acid (DPA) is a ω-3 fatty acid found in fish oils. 17-oxo-7(Z),10(Z),13(Z),15(E),19(Z)-docosapentaenoic acid is a metabolite of lipoxygenase-mediated oxidation of DPA that is produced endogenously by aspirin-enhanced COX-2 activity. It has been shown to activate Nrf2-dependent antioxidant gene expression, to act as a PPARγ agonist (EC50 = ~200 nM), and to inhibit pro-inflammatory cytokine and nitric oxide production at biological concentration ranges (5-25 μM).

Epoxide hydrolases convert the EETs into vicinal diols, with the concurrent loss of much of their biological activity. The 8(S),9(R)-EET isomer is metabolized by platelet COX to form 8(S),9(R),11(R)-THETA, a trihydroxy fatty acid which may act as a renal vasoconstrictor.

17-oxo-4(Z),7(Z),10(Z),13(Z),15(E),19(Z)-Docosahexaenoic acid is a metabolite of lipoxygenase-mediated oxidation of DHA that is produced endogenously by aspirin-enhanced COX-2 activity. It has been shown to activate Nrf2-dependent antioxidant gene expression, to act as a PPARγ agonist (EC50 = ~200 nM), and to inhibit pro-inflammatory cytokine and nitric oxide production at biological concentration ranges (5-25 μM).

9(Z)-Pentacosene is a cuticular hydrocarbon and insect sex hormone.1,2,3 It is found in the cuticle of female F. canicularis flies and is an attractant to males in a trap assay.1 9(Z)-Pentacosene is a contact sex hormone in scarab beetles and locust borers that is more abundant in females than males.2,3 It elicits arrestment, alignment, and mounting by males of both species in mating assays but only elicits copulation by the locust borer. 9(Z)-Pentacosene is also produced by the orchid O. exaltata and by C. cunicularius, a pollinator of O. exaltata.4

9(Z),12(Z),15(Z),18(Z),21(Z)-Tetracosapentaenoic acid is an ω-3 very long-chain polyunsaturated fatty acid. It has been used to study the desaturation and elongation of ω-3 polyunsaturated fatty acids. It is elongated to form C26:5 or acted on by δ6 desaturase to form C24:6. 9(Z),12(Z),15(Z),18(Z),21(Z)-Tetracosapentaenoic acid is found at low levels in mouse brain and spleen and levels decrease in the brain and spleen of old and exceptionally old mice.

9(E),11(E),13(E)-Octadecatrienoic acid (β-ESA) is a conjugated polyunsaturated fatty acid that is found in plant seed oils and in mixtures of conjugated linolenic acids synthesized by the alkaline isomerization of linolenic acid. It reduces growth of Caco-2 colon cancer cells in a dose-dependent and time-dependent manner. In vitro, β-ESA induces DNA fragmentation and upregulation of pro-apoptotic Bax mRNA. β-ESA decreases protein expression of the apoptosis suppression factor Bcl-2 and induces apoptosis in T24 bladder cancer cells via production of reactive oxygen species. It also inhibits bacterial fatty acid dioxygenase with a Ki value of 49 nM in vitro.

MMP-9-IN-8 (Compound 3), an MMP-9 inhibitor, exhibits inhibitory activities of 42.16% at 10 μM and 58.28% at 50 μM. Additionally, MMP-9-IN-8 demonstrates anti-cancer properties, inducing apoptosis in MCF-7 cells with an IC50 value of 23.42 μM [1].

Compound 9, 15-Nor-14-oxolabda-8(17),12E-diene-18-oic acid, is an isolated compound derived from the roots of Chloranthus spicatus [1].

8-Acetoxy-15,16-epoxy-8,9-secolabda-13(16),14-diene-7,9-dione is a natural product for research related to life sciences. The catalog number is TN5610 and the CAS number is 76497-89-7.

E,Z-Platanoside is a natural product for research related to life sciences. The catalog number is TN5512 and the CAS number is 1197343-17-1.

9(Z),11(E),13(E)-Octadecatrienoic Acid (α-ESA) is a conjugated polyunsaturated fatty acid commonly found in plant seed oil. This fatty acid accounts for about 60% of the total fatty acid composition of bitter gourd seed oil and about 70% in tung oil. α-ESA is metabolized and converted to conjugated linoleic acid (9Z,11E-CLA) in rats. It has shown potential as a tumor growth suppressor. In colon cancer Caco-2 cells, α-ESA induced apoptosis through up-regulation of GADD45, p53, and PPARγ. In DLD-1 cells supplemented with α-ESA, apoptosis was induced via lipid peroxidation with an EC50 of 20 μM. It also inhibits DNA polymerases and topoisomerases with IC50s ranging from ~5-20 μM for different isoforms of the enzymes.

10-Isobutyryloxy-8,9-epoxythymol isobutyrate is a major constituent of Inula helenium and Inula royleana root cultures.

(Z)-9-nonadecene (9-Nonadecene) was identified the first time in T. melanocephalum. (Z)-9-nonadecene is a major component in mandibular glands and iridodials are produced in pygidial glands.

9,13β-Epidioxy-8(14)-abieten-18-oic acid has anti-inflammatory activities, it exhibits moderate activities on NO levels in LPS-stimulated murine microglia BV2 cells, with IC50 values of 57.3 ± 0.2 uM. It is also a potential antitumor-promoting diterpenoid, it shows potent inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol 13-acetate. 9 α ,13 β -Epidioxyabeit-8(14)en-18-oic acid may contribute to the growth inhibitory effect of the pine needles and may play an important role in the allelopathy of red pine.

8-Hydroxy-9,10-diisobutyryloxy-thymol, a potent terpenoid found in Inula sericophylla [1], exhibits significant bioactivity.

17(13→14)-Abeo-ent-3S*,13S*,16-trihydroxystrob-8(15)-ene is a sesquiterpene lactone of natural origin that exhibits anti-inflammatory properties [1].

9(E),11(E)-12-nitro Conjugated linoleic acid (9(E),11(E)-12-nitro CLA) is a nitrated fatty acid. It is formed from 9(Z),11(E)-CLA upon exposure to acidified nitrite, peroxynitrite, gaseous nitrogen dioxide, or a combination of myeloperoxidase, hydrogen peroxide, and nitrite.1It is also formed in LPS-stimulated RAW 264.7 macrophages, an effect that can be reduced by the nitric oxide synthase (NOS) inhibitor L-NAME .29(E),11(E)-12-nitro CLA has been found in human plasma. 1.Woodcock, S.R., Salvatore, S.R., Bonacci, G., et al.Biomimetic nitration of conjugated linoleic acid: Formation and characterization of naturally occurring conjugated nitrodienesJ. Org. Chem.79(1)25-33(2014) 2.Bonacci, G., Baker, P.R.S., Salvatore, S.R., et al.Conjugated linoleic acid is a preferential substrate for fatty acid nitrationJ. Biol. Chem.287(53)44071-44082(2012)

5(Z),8(Z),14(Z)-Eicosatrienoic acid is a polyunsaturated fatty acid that can be a substrate for 5-lipoxygenase (5-LO). 5-LO from RBL-1 cells converts this fatty acid to 5-hydroxy-6,8,14-eicosatrienoic acid and 5-hydroperoxy-6,8,14-eicosatrienoic acid. Due to the lack of a double bond at C-11, this particular fatty acid cannot be used in leukotriene A formation.

9-Deacetyltaxinine E is a natural product from Taxus mairei.

ent-11alpha-Hydroxyabieta-8(14),13(15)-dien-16,12alpha-olide shows significant cytotoxic activity against ANA-1 and Jurkat cells with IC50 values 7.12 x 10(-3) and 1.79 x 10(-2) microM.

(E/Z)-Eltrombopag 13C4 ((E/Z)-SB-497115 13C4) is a mixture complex of E-Eltrombopag and Z-Eltrombopag, with 13C labeled. Z-Eltrombopag is a thrombopoietin (TPO) receptor agonist developed for certain conditions that lead to thrombocytopenia.

Nucleoside Derivatives - Xylo-nucleosides; 8-Modified purine nucleosides; Amino nucleosides; N-Methylated alkylated nucleosides

3-Cyanovinyl-9-(5’-O-(4,4’-dimethoxytrityl)-2’-deoxyribofuranosyl)carbazole (trans: CAS#1044273-26-8) is a useful organic compound for research related to life sciences and the catalog number is TNU0955.

TLR7/8 agonist 9 (Compound 25a), exhibiting EC50 values of 40 nM and 23 nM for hTLR7 and hTLR8 respectively, demonstrates anti-tumor properties and enhances the efficacy of PD-1/PD-L1 blockade treatments. This compound is utilized in cancer immunotherapy research [1].

13-Oxopodocarp-8(14)-en-18-oic acid is a natural product for research related to life sciences. The catalog number is TN2619 and the CAS number is 63976-69-2.

(E/Z)-BCI (NSC-150117), a dual-specificity phosphatase 6 (DUSP6) inhibitor with anti-inflammatory properties, reduces LPS-induced inflammatory mediators and ROS production in macrophage cells by activating the Nrf2 signaling axis and inhibiting the NF-κB pathway.

Mead acid, a 20-carbon ω-9 polyunsaturated fatty acid, experiences elevated levels in human plasma under conditions of essential fatty acid deficiency. As 1,25(Z),8(Z),11(Z)-Eicosatrienoic Acid methyl ester (Mead acid methyl ester), it frequently serves as a standard for fatty acid analysis, particularly after fatty acids have been transesterified into methyl esters.

10(E),12(Z)-Conjugated linoleic acid methyl ester serves as a standard for quantifying 10(E),12(Z)-conjugated linoleic acid in L. plantarum culture samples. [Matreya, LLC. Catalog No. 1254]

(Z)-9-Propenyladenine is a mutagenic impurity in tenofovir disoproxil fumarate.

1-Amino-8-benzyloxy-9-(b-D-xylofuranosyl)guanine is a Nucleoside Derivative - Xylo-nucleoside; 8-Modified purine nucleoside; Amino nucleoside.

2-Methoxyfuranoguaia-9-ene-8-one is a natural product for research related to life sciences. The catalog number is TN6585 and the CAS number is 88010-62-2.

Eltrombopag Olamine (Eltrombopag diethanolamine salt) is the orally active ethanolamine salt of eltrombopag, a small-molecule, nonpeptide thrombopoietin receptor agonist with megakaryopoiesis-stimulating activity. Eltrombopag binds to and stimulates the transmembrane domain of the platelet thrombopoietin receptor (TPO-R or CD110), a member of the hematopoietin receptor superfamily. Activation of TPO-R leads to the proliferation and differentiation of cells in the megakaryocytic lineage and an increase in platelet production.

Eltrombopag (SB-497115-GR), an orally active thrombopoietin receptor agonist with megakaryopoiesis stimulating activity, binds to and stimulates the platelet thrombopoietin receptor (TPO-R or CD110).