Methyl 12-methyltridecanoate Reference: M1657-20 In the milk of cows 12-methyltridecanoic acid and its isomers are some of the most common odd- and branched-chain fatty acids.1 In bacteria iso-fatty acid2 content and composition can often be used as a taxonomic marker3 because iso-fatty acids are often found in bacteria but not commonly in other microorganisms. Some bacteria have iso- but not anteiso-fatty acids while others have anteiso- but not iso-fatty acids. Iso-fatty acids are found in small amounts in marine organisms and ruminants, mainly due to the food chain but also due to some de novo synthesis. Iso-fatty acids with a total even number of carbons are more common than a total odd number. Some waxy materials such as lanolin, as well as secretions near animal eyes, contain an unusually high amount of iso-fatty acids being employed for their lubricating effect. Branched chain fatty acids are critical for the regulation of fluidity in membranes and in membrane transport for many types of bacteria due to their having a significantly lower transition temperature than straight chain fatty acids. Some bacteria handle stress (such as heat and toxicity) by changing the ratio of anteiso/iso-fatty acids in the cell membrane. Iso-fatty acids have been found to be activators for various enzymes and systems and are used as protein modifiers. Although iso-even chain fatty acids are commonly derived from isobutyryl-CoA some bacteria derive all iso-even chain fatty acids via alpha-oxidation of iso-odd chain fatty acids.4 Although iso-fatty acids are not usually found in plant oils the waxy surface of leaves can contain significant amounts of these fatty acids.
2-Hydroxy Methyl Ester Mixture Reference: M1722-1 This fatty acid mixture contains common alpha-hydroxy fatty acids in methylene chloride for the quantitative identification and quantitation of unknowns. Microbial fatty acid profiles are unique from one species to another and can therefore be used in the determination of bacterial identity. All materials are analyzed to verify their identity and to determine their purity. All analytes are 98+% pure. This standard is accurately prepared by gravimetric technique (+/- 0.5%) and all glassware is class A rated. Ampules are purged with nitrogen/argon before and after filling and chilled before being flame sealed. Store ampules sealed as received and process without delay immediately after opening the ampule. Composition: Contains the methyl esters of the following 2-hydroxy fatty acids.,C14:0, 20.0%,C16:0, 20.0%,C18:0, 15.0%,C20:0, 15.0%,C22:0, 10.0%,C23:0, 10.0%,C24:0, 10.0%
3-Hydroxytridecanoic acid Reference: M1733-25 This 3-hydroxytridecanoic acid is a high purity standard that is ideal for analysis and biological systems. 3- Hydroxytridecanoic acid is unusual in many biological systems and is therefore useful as an internal standard.1 However 3- hydroxytridecanoic acid is a major constituent of some organisms such as in the anaerobic bacterium Veillonella2 3-Hydroxy fatty acids are intermediates in fatty acid biosynthesis and have been found to be converted to the omega-fatty acid by the enzyme CYP4F11 and then into dicarboxylic acids in vivo.3 3-Hydroxy fatty acids are used as biomarkers for fatty acid oxidative disorders of both the long- and short-chain 3-hydroxy-acyl-CoA dehydrogenases.4 Polyhydroxyalkenoates, polyesters produced by bacteria fermentation, are used for carbon and energy storage and are of interest in studies regarding their synthesis, properties and mechanisms and are used as biodegradable plastics.5 Medium chain-length polyhydroxyalkenoate monomers may have pharmaceutical properties.
lyso-Sulfatide (NH4+salt) Reference: M1904-1 Lyso-Sulfatide is ideal for the preparation of well-defined and labeled sulfatides and is excellent for enzyme and metabolism research. Sulfatide is a type of sulfolipid that is found primarily in the central nervous system and is a myelin-specific sphingolipid. A deficiency of sulfatide in white and gray matter has been associated with Alzheimer’s disease and other types of dementia. Apoliprotein E plays an important regulating role in the metabolism of sulfatides.1 A production of anti-sulfatide antibodies in the cerebrospinal fluid, leading to a deficiency in sulfatides, may be a cause of degeneration of the myelin sheath, leading to multiple sclerosis.2 Metachromatic leukodystrophy is an inherited disorder characterized by a deficiency of the lysosomal enzyme arylsulfatase A and the subsequent accumulation of sulfatide in neural and visceral tissues.3 An immunomodulatory role for sulfatides has been suggested in the pathogenesis of tuberculosis.
N-Octadecanoyl-D35-psychosine, (perdeuterated, C18:0 fatty acid) Reference: M1914-5 This cerebroside product is a glycosphingolipid containing a galactose (galactocerebroside) attached to a ceramide acylated with a C18:0 perdeuterated fatty acid, making it an ideal standard for mass spectrometry. Galactocerebrosides are found primarily in neuronal tissues and are the major glycosphingolipids in the central nervous system. They are the largest single component of the myelin sheath of nerves and seem to act, along with other molecules, to form part of the structural support of the myelin sheath.1 Cerebrosides are involved in a very wide range of biological activities such as cell agglutination, intracellular communication, cellular development, and antitumor/cytotoxic effects.2 Galactocerebroside can be metabolized into sulfatide which is also abundant in the nervous system and myelin sheaths. Due to the relatively high melting point of cerebrosides (much greater than physiological body temperature) they have a para-crystalline structure. Krabbe’s disease (globoid cell leukodystrophy) is characterized by a deficiency in the enzyme galactocerebrosidase, which is responsible for degrading galactocerebroside. This leads to an accumulation of cerebroside and psychosine (which is very cytotoxic and can result in demyelination of nerves and loss of axonal conductivity). This standard from Matreya is excellent for use in the identification and isolation of cerebrosides in the study of Krabbe’s disease and other studies.3 Composition: Deuterium labeled stearoyl sidechain
N-Heptadecanoyl-sulfatide Reference: M1934-1 This product is a well-defined sulfatide containing a heptadecanoyl group acylated to the amine of the sphingosine and is ideal as an internal standard.1 Sulfatide is a type of sulfolipid that is found primarily in the central nervous system and is a myelin-specific sphingolipid. A deficiency of sulfatide in white and gray matter has been associated with Alzheimer’s disease and other types of dementia. Apoliprotein E plays an important regulating role in the metabolism of sulfatides.2 The production of anti-sulfatide antibodies in the cerebrospinal fluid, leading to a deficiency in sulfatides, may be a cause of degeneration of the myelin sheath, leading to multiple sclerosis and other demyelinating diseases.3 Metachromatic leukodystrophy is an inherited disorder characterized by a deficiency of the lysosomal enzyme arylsulfatase A and the subsequent accumulation of sulfatide in neural and visceral tissues.4 Sulfatide also regulates the differentiation of oligodendroblasts. Central nervous system (CNS) myelin is strongly inhibitory to growing axons and sulfatides present in the myelin of the CNS have been identified as major myelin-associated axon growth inhibitors.5 A low level of serum sulfatides has been linked with an increased risk of cardiovascular disease in some situations. Sulfatides in the myelin, especially cistetracosenoyl- sulfatides, stimulate a distinct population of CD1d-restricted natural killer T cells giving these sulfatides important implications for the design of therapeutics that target T cells reactive for myelin glycolipids in autoimmune diseases of the central nervous system.6
N-Dodecanoyl-sulfatide Reference: M1938-1 This product is a well-defined sulfatide containing a dodecanoic acid acylated to the amine of the sphingosine and is ideal as an internal standard. Sulfatide is a type of sulfolipid that is found primarily in the central nervous system and is a myelinspecific sphingolipid. A deficiency of sulfatide in white and gray matter has been associated with Alzheimer’s disease and other types of dementia. Apoliprotein E plays an important regulating role in the metabolism of sulfatides.1 The production of anti-sulfatide antibodies in the cerebrospinal fluid, leading to a deficiency in sulfatides, may be a cause of degeneration of the myelin sheath, leading to multiple sclerosis and other demyelinating diseases.2 Metachromatic leukodystrophy is an inherited disorder characterized by a deficiency of the lysosomal enzyme arylsulfatase A and the subsequent accumulation of sulfatide in neural and visceral tissues.3 Sulfatide also regulates the differentiation of oligodendroblasts. Central nervous system (CNS) myelin is strongly inhibitory to growing axons and sulfatides present in the myelin of the CNS have been identified as major myelin-associated axon growth inhibitors.4 A low level of serum sulfatides has been linked with an increased risk of cardiovascular disease in some situations. Sulfatides in the myelin, especially cis-tetracosenoyl-sulfatides, stimulate a distinct population of CD1d-restricted natural killer T cells giving these sulfatides important implications for the design of therapeutics that target T cells reactive for myelin glycolipids in autoimmune diseases of the central nervous system.5
FIM-FAME-6 Mixture (Methyl ester mixture) Reference: M2009-1 This fatty acid mixture contains saturated and mono and polyunsaturated fatty acids in heptane for the qualitative identification and quantitation of unknowns. Microbial fatty acid profiles are unique from one species to another and can therefore be used in the determination of bacterial identity. All materials are analyzed to verify their identity and to determine their purity. All analytes are 98+% pure. This standard is accurately prepared by gravimetric technique (+/- 0.5%) and all glassware is class A rated. Ampules are purged with nitrogen/argon before and after filling and chilled before being flame sealed. Store ampules sealed as received and process without delay immediately after opening the ampule. Composition: Each methyl ester is 3.03% of the mixture except C16:0, which is 6.06%.,C4:0,C6:0,C8:0,C10:0,C11:0,C12:0,C13:0,C14:0,C14:1(cis-9),C15:0,C15:1(cis-10),C16:0,C16:1(cis-9),C17:0,C17:1(cis-10),C18:0,C18:1(trans-9),C18:1(cis-9),C18:2(all-cis-9,12),C20:0,C18:3(all-cis 6,9,12),C20:1(cis-11),C18:3(all-cis 9,12,15),C20:2(all-cis 11,14),C22:0,C20:3(all-cis 8,11,14),C22:1(cis 13),C20:3(all-cis 11,14,17),C20:4(all-cis 5,8,11,14),C22:2(all-cis 13,16),C24:1(cis-15),C22:6(all-cis 4,7,10,13,16,19),listed in order of their elution.
FIM-FAME-7 Mixture (Methyl ester mixture) Reference: M2010-1 This fatty acid methyl ester mixture contains 37 fatty acids for the identification and quantification of unknowns.1 It is prepared from high purity stock material and contains saturated and unsaturated fatty acids. This mixture is very useful for bacterial identification,2 triglyceride determination and the analysis of various plant and animal lipids.3 Understanding the role of fatty acids and fatty acid metabolism in plants and animals is important in drug development. Composition: Contains the methyl esters of these fatty acids:,C4:0, 4.0%,C6:0, 4.0%,C8:0, 4.0%,C10:0, 4.0%,C11:0, 2.0%,C12:0, 4.0%,C13:0, 2.0%,C14:0, 4.0%,C14:1(cis-9), 2.0%,C15:0, 2.0%,C15:1(cis-10), 2.0%,C16:0, 6.0%,C16:1(cis-9), 2.0%,C17:0, 2.0%,C17:1(cis-10), 2.0%,C18:0, 4.0%,C18:1(trans-9), 2.0%,C18:1(cis-9), 4.0%,C18:2(all-trans-9,12), 2.0%,C18:2(all-cis-9,12), 2.0%,C20:0, 4.0%,C18:3(all-cis 6,9,12), 2.0%,C20:1(cis-11), 2.0%,C18:3(all-cis 9,12,15), 2.0%,C21:0, 2.0%,C20:2(all-cis 11,14,), 2.0%,C22:0, 4.0%,C20:3 (all-cis 8,11,14, 2.0%,C22:1(cis 13), 2.0%,C20:3(all-cis 11,14,17), 2.0%,C20:4(all-cis 5,8,11,14), 2.0%,C23:0, 2.0%,C22:2(all-cis 13,16), 2.0%,C24:0, 4.0%,C20:5(all-cis 5,8,11,14,17), 2.0%,C24:1(cis-15), 2.0%,C22:6(all-cis 4,7,10,13,16,19), 2.0%,listed in order of their elution.
Long Chain Fatty Acid Methyl Ester Mixture Reference: M2011-1 Very-long-chain fatty acids (VLCFA) consisting of 26 carbons or more comprise a small but very important group of biological lipids that are found in both plants and animals. There is relatively little known about VLCFA, especially those with more than 30 carbons, and the need for high purity standards to explore their mechanisms and processes is greatly needed. VLCFA are found in small amounts in most animal tissues and are especially abundant in the brain, skin, testis, and some glands, such as the meibomian gland. The recognition of VLCFA in human diseases has recently sparked a renewed interest in the investigation of these crucial compounds. VLCFA are implicated in several diseases and standards for the determination of the lipids associated with these diseases are needed. One of these human diseases, X-linked adrenoleukodystrophy, causes an increase in plasma of VLCFA due to a genetic defect that affects the peroxisomal assembly and contributes to severe pathological changes such as inflammatory responses; This disease can also lead to neurological changes and severe demyelination. Another disease that results in unusually high levels of VLCFA is Zwelleger syndrome which is characterized by a reduced number of, and morphologically-abnormal, peroxisomes.1 In plants VLCFA are converted to long chain hydrocarbons which are used to make waxes that are essential to their survival.2,3 VLCFA acylated to sphingolipids are critical in many biological functions4 and substantial amounts are found to be amide-linked to the long-chain sphingoid base sphinganine, forming a ceramide, which constitutes the lipid backbone of sphingomyelin and other sphingolipids. VLCFA can often be found in esterified linkages with cholesterol, gangliosides, galactocerebrosides, sphingomyelin, and phosphatidylcholine. In myelin VLCFA are important in increasing the structural stability. Lipids are very important in signaling and the influence of VLCFA in signaling needs to be further explored.5 Studies that explore the roles of VLCFA acylated to phospholipids, sphingolipids and glycerolipids or esterified to triglycerides, sterols, and other compounds show great promise in revealing much about the various biological functions of these lipids. If you require VLCFA acylated or esterified to a specific backbone the team at Matreya will be happy to synthesize them for you. Composition: Quantitative mix contains:,C24:0, 20.0%,C26:0, 20.0%,C28:0, 20.0%,C30:0, 20.0%,C32:0, 20.0%
FIM-FAME-8 Mixture Reference: M2012-1 This FAME mixture contains 5 fatty acid methyl esters for the identification and quantification of unknowns.1 It is prepared from high purity stock material and contains saturated and unsaturated fatty acids in the 18 carbon series. This mixture is very useful for bacterial identification,2 triglyceride determination and the analysis of various plant and animal lipids.3 Understanding the role of fatty acids and fatty acid metabolism in plants and animals is important in drug development. Composition: C18:0, Methyl octadecanoate (stearate) [20.0%],C18:1, Methyl octadecenoate (cis-9) (oleate) [20.0%],C18:2, Methyl octadecadienoate (all cis-9,12) (linoleate) [20.0%],C18:3, Methyl octadecatrienoate (all cis-9,12,15) (linolenate) [20.0%],C18:4, Methyl stearidonate (all cis-6,9,12,15) (moroctic acid methyl ester) [20.0%],listed in order of their elution.
N-omega-CD3-Octadecanoyl monosialoganglioside GM1 (NH4+ salt) Reference: M2050-500 Gangliosides1 are acidic glycosphingolipids that form lipid rafts in the outer leaflet of the cell plasma membrane, especially in neuronal cells in the central nervous system.2 They participate in cellular proliferation, differentiation, adhesion, signal transduction, cell-to-cell interactions, tumorigenesis, and metastasis.3 The accumulation of gangliosides has been linked to several diseases including Tay-Sachs and Sandhoff disease while an autoimmune response against gangliosides can lead to Guillain-Barre syndrome. GM1 stimulates neuronal sprouting and enhances the action of nerve growth factor (NGF) by directly and tightly associating with Trk, the high-affinity tyrosine kinase-type receptor for NGF. It is the specific cell surface receptor for cholera toxin.4 This deuterated ganglioside is ideal for the identification of gangliosides in samples and biological systems using mass spectrometry or HPLC.5