2.0 2012-08-03 14:57:54 -0600 2015-09-13 15:15:32 -0600 ECMDB21398 M2MDB001793 Levulinic acid Levulinic acid is a crystalline keto acid prepared from levulose, inulin, starch, etc., by boiling them with dilute hydrochloric or sulfuric acids. 3-Acetylpropionate 3-Acetylpropionic acid 4-Ketovalerate 4-Ketovaleric acid 4-Oxopentanoate 4-Oxopentanoic acid 4-Oxovalerate 4-Oxovaleric acid B-Acetylpropionate B-Acetylpropionic acid Beta-Acetylpropionate Beta-Acetylpropionic acid G-Ketovalerate G-Ketovaleric acid Gamma-Ketovalerate Gamma-Ketovaleric acid Laevulinate Laevulinic acid Levulate Levulic acid Levulinate β-Acetylpropionate β-Acetylpropionic acid γ-Ketovalerate γ-Ketovaleric acid C5H8O3 116.1152 116.047344122 4-oxopentanoic acid levulinic acid 123-76-2 CC(=O)CCC(O)=O InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8) JOOXCMJARBKPKM-UHFFFAOYSA-N Liquid Cytoplasm logp -0.14 ALOGPS logs 0.08 ALOGPS solubility 1.39e+02 g/l ALOGPS melting_point 30-33 oC logp -0.069 ChemAxon pka_strongest_acidic 4.32 ChemAxon pka_strongest_basic -7.3 ChemAxon iupac 4-oxopentanoic acid ChemAxon average_mass 116.1152 ChemAxon mono_mass 116.047344122 ChemAxon smiles CC(=O)CCC(O)=O ChemAxon formula C5H8O3 ChemAxon inchi InChI=1S/C5H8O3/c1-4(6)2-3-5(7)8/h2-3H2,1H3,(H,7,8) ChemAxon inchikey JOOXCMJARBKPKM-UHFFFAOYSA-N ChemAxon polar_surface_area 54.37 ChemAxon refractivity 27.09 ChemAxon polarizability 11.23 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 970 Specdb::CMs 980 Specdb::CMs 6213 Specdb::CMs 27919 Specdb::CMs 29733 Specdb::CMs 29741 Specdb::CMs 31212 Specdb::CMs 31213 Specdb::CMs 37720 Specdb::CMs 172891 Specdb::CMs 1072757 Specdb::CMs 1072759 Specdb::CMs 1072760 Specdb::CMs 1072761 Specdb::CMs 1072763 Specdb::NmrOneD 1499 Specdb::NmrOneD 7462 Specdb::NmrOneD 7463 Specdb::NmrOneD 7464 Specdb::NmrOneD 7465 Specdb::NmrOneD 7466 Specdb::NmrOneD 7467 Specdb::NmrOneD 7468 Specdb::NmrOneD 7469 Specdb::NmrOneD 7470 Specdb::NmrOneD 7471 Specdb::NmrOneD 7472 Specdb::NmrOneD 7473 Specdb::NmrOneD 7474 Specdb::NmrOneD 7475 Specdb::NmrOneD 7476 Specdb::NmrOneD 7477 Specdb::NmrOneD 7478 Specdb::NmrOneD 7479 Specdb::NmrOneD 7480 Specdb::NmrOneD 7481 Specdb::MsMs 1011 Specdb::MsMs 1012 Specdb::MsMs 1013 Specdb::MsMs 4544 Specdb::MsMs 246117 Specdb::MsMs 246118 Specdb::MsMs 246119 Specdb::MsMs 266061 Specdb::MsMs 266062 Specdb::MsMs 266063 Specdb::MsMs 2244752 Specdb::MsMs 2246856 Specdb::MsMs 2247413 Specdb::MsMs 2269810 Specdb::MsMs 2269811 Specdb::MsMs 2269812 Specdb::MsMs 3072186 Specdb::MsMs 3072187 Specdb::MsMs 3072188 Specdb::NmrTwoD 1445 HMDB00720 11579 11091 SHF Levulinic acid Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776 Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. 9869358 Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. 12829005 Lopez Montes A, Lorenzo I, Perez Martinez J: [Porphyria and inappropriate antidiuretic hormone syndrome] Nefrologia. 2004;24 Suppl 3:85-8. 15219077 Melgaard B, Clausen J, Rastogi SC: Heavy metal levels and delta-amino-levulinic acid dehydrase levels in peripheral polyneuropathy. Acta Neurol Scand. 1976 Apr;53(4):291-307. 178141 Matsui M, Kaji R, Oka N, Nishio T, Kimura J: [Multifocal axonal motor neuropathy associated with anti-ganglioside antibodies] Rinsho Shinkeigaku. 1992 Oct;32(10):1130-5. 1297559 Keithly L, Ferris Wayne G, Cullen DM, Connolly GN: Industry research on the use and effects of levulinic acid: a case study in cigarette additives. Nicotine Tob Res. 2005 Oct;7(5):761-71. 16191747 Endo G, Horiguchi S, Kiyota I: Urinary N-acetyl-beta-D-glucosaminidase activity in lead-exposed workers. J Appl Toxicol. 1990 Aug;10(4):235-8. 2391405 Cai, Lei; Lu, Xiuyang; He, Long; Xia, Wenli; Ren, Qilong. Review on preparation methods of levulinic acid, a new platform chemical. Xiandai Huagong (2003), 23(4), 14-16. http://hmdb.ca/system/metabolites/msds/000/000/639/original/HMDB00720.pdf?1358894736 48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L Gluco Bioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h 1260.0 uM 0.0 37 oC BW25113 Stationary Phase, glucose limited 5040000 0 Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. 17379776