1.0 2010-04-08 22:07:12 UTC 2025-11-18 23:02:17 UTC FDB006586 Proazulene Proazulene, also known as matricine, is a member of the class of compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Thus, proazulene is considered to be an isoprenoid lipid molecule. Proazulene is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Proazulene can be found in anise, which makes proazulene a potential biomarker for the consumption of this food product. Chamazulene, a blue-violet derivative of azulene, found in a variety of plants including in chamomile (Matricaria chamomilla), wormwood (Artemisia absinthium) and yarrow (Achillea millefolium) is biosynthesized from matricin . C17H22O5 306.358 306.146723808 (3S,3aR,4S,9R,9aS,9bS)-9-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate matricin 29041-35-8 [H][C@@]1(C)C(=O)O[C@]2([H])[C@]3([H])C(C=C[C@@]3(C)O)=C(C)C[C@]([H])(OC(C)=O)[C@@]12[H] InChI=1S/C17H22O5/c1-8-7-12(21-10(3)18)13-9(2)16(19)22-15(13)14-11(8)5-6-17(14,4)20/h5-6,9,12-15,20H,7H2,1-4H3/t9-,12-,13+,14-,15-,17+/m0/s1 SYTRJRUSWMMZLV-VQGWEXQJSA-N belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Gamma butyrolactones Organic compounds Organoheterocyclic compounds Lactones Gamma butyrolactones Aliphatic heteropolycyclic compounds Carbonyl compounds Carboxylic acid esters Dicarboxylic acids and derivatives Hydrocarbon derivatives Organic oxides Oxacyclic compounds Tertiary alcohols Tetrahydrofurans Alcohol Aliphatic heteropolycyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dicarboxylic acid or derivatives Gamma butyrolactone Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Oxacycle Tertiary alcohol Tetrahydrofuran Guaiane sesquiterpenoids Guaiane sesquiterpenoids Sesquiterpenoids (C15) sesquiterpene lactone logp 1.84 ALOGPS logs -2.53 ALOGPS solubility 8.96e-01 g/l ALOGPS logp 0.72 ChemAxon pka_strongest_acidic 14.24 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac (3S,3aR,4S,9R,9aS,9bS)-9-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,9H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate ChemAxon average_mass 306.358 ChemAxon mono_mass 306.146723808 ChemAxon smiles [H][C@@]1(C)C(=O)O[C@]2([H])[C@]3([H])C(C=C[C@@]3(C)O)=C(C)C[C@]([H])(OC(C)=O)[C@@]12[H] ChemAxon formula C17H22O5 ChemAxon inchi InChI=1S/C17H22O5/c1-8-7-12(21-10(3)18)13-9(2)16(19)22-15(13)14-11(8)5-6-17(14,4)20/h5-6,9,12-15,20H,7H2,1-4H3/t9-,12-,13+,14-,15-,17+/m0/s1 ChemAxon inchikey SYTRJRUSWMMZLV-VQGWEXQJSA-N ChemAxon polar_surface_area 72.83 ChemAxon refractivity 80.54 ChemAxon polarizability 32.31 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 104799 Specdb::MsMs 104800 Specdb::MsMs 104801 Specdb::MsMs 171144 Specdb::MsMs 171145 Specdb::MsMs 171146 Specdb::MsMs 3603113 Specdb::MsMs 3603114 Specdb::MsMs 3603115 Specdb::MsMs 3603116 Specdb::MsMs 3603117 Specdb::MsMs 3603118 Anise Type 1 specific Pimpinella anisum 271192