1.0 2010-04-08 22:07:10 UTC 2025-11-18 23:02:01 UTC FDB006482 Myristolic acid Myristoleic acid, also known as 9-tetradecenoic acid or (9z)-tetradecenoate, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, myristoleic acid is considered to be a fatty acid lipid molecule. Myristoleic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Myristoleic acid can be found in a number of food items such as lichee, sauce, sesame, and loquat, which makes myristoleic acid a potential biomarker for the consumption of these food products. Myristoleic acid can be found primarily in blood, feces, and saliva, as well as in human adipose tissue tissue. Myristoleic acid exists in all eukaryotes, ranging from yeast to humans. Myristoleic acid, or 9-tetradecenoic acid, is an omega-5 fatty acid. It is biosynthesized from myristic acid by the enzyme Stearoyl-CoA desaturase-1, but it is uncommon in nature. One of the major sources of this fatty acid is the seed oil from plants of the family Myristicaceae, comprising up to 30 per cent of the oil in some species. It is a constituent of Serenoa or Saw palmetto, and appears to have activity against LNCaP prostate-cancer cells. It also comprises 1.89% of the fats from the fruit of the durian species Durio graveolens . C14H26O2 226.355 226.193280076 (9Z)-tetradec-9-enoic acid myristoleic acid 544-64-9 CCCC\C=C/CCCCCCCC(O)=O InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5- YWWVWXASSLXJHU-WAYWQWQTSA-N belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Long-chain fatty acids Organic compounds Lipids and lipid-like molecules Fatty Acyls Fatty acids and conjugates Aliphatic acyclic compounds Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Straight chain fatty acids Unsaturated fatty acids Aliphatic acyclic compound Carbonyl group Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Long-chain fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Straight chain fatty acid Unsaturated fatty acid Monounsaturated fatty acids Unsaturated fatty acids Unsaturated fatty acids long-chain fatty acid tetradecenoic acid logp 5.69 ALOGPS logs -5.00 ALOGPS solubility 2.24e-03 g/l ALOGPS logp 5.01 ChemAxon pka_strongest_acidic 4.99 ChemAxon iupac (9Z)-tetradec-9-enoic acid ChemAxon average_mass 226.355 ChemAxon mono_mass 226.193280076 ChemAxon smiles CCCC\C=C/CCCCCCCC(O)=O ChemAxon formula C14H26O2 ChemAxon inchi InChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5- ChemAxon inchikey YWWVWXASSLXJHU-WAYWQWQTSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 69 ChemAxon polarizability 28.75 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::EiMs 1604 Specdb::MsMs 88008 Specdb::MsMs 88009 Specdb::MsMs 88010 Specdb::MsMs 150642 Specdb::MsMs 150643 Specdb::MsMs 150644 Specdb::MsMs 438124 Specdb::MsMs 438125 Specdb::MsMs 438126 Specdb::MsMs 438127 Specdb::MsMs 438665 Specdb::MsMs 2353204 Specdb::MsMs 2353205 Specdb::MsMs 2353206 Specdb::MsMs 2585905 Specdb::MsMs 2585906 Specdb::MsMs 2585907 Specdb::CMs 2649 Specdb::CMs 38216 Specdb::CMs 168144 Specdb::NmrOneD 327232 Specdb::NmrOneD 327233 Specdb::NmrOneD 327234 Specdb::NmrOneD 327235 Specdb::NmrOneD 327236 Specdb::NmrOneD 327237 Specdb::NmrOneD 327238 Specdb::NmrOneD 327239 Specdb::NmrOneD 327240 Specdb::NmrOneD 327241 Specdb::NmrOneD 327242 Specdb::NmrOneD 327243 Specdb::NmrOneD 327244 Specdb::NmrOneD 327245 Specdb::NmrOneD 327246 Specdb::NmrOneD 327247 Specdb::NmrOneD 327248 Specdb::NmrOneD 327249 Specdb::NmrOneD 327250 Specdb::NmrOneD 327251 HMDB0002000 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Parsley Type 1 specific Petroselinum crispum 4043 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823