Acet-oxy-γ-valerolactone.
Ontology highlight
ABSTRACT:
SUBMITTER: Tristram C
PROVIDER: S-EPMC3685093 | biostudies-literature |
REPOSITORIES: biostudies-literature
Similar Datasets
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Project description:The title compound, C(17)H(22)O(6), was semi-synthesized from 9-hy-droxy-arthenolide, which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule contains fused five- and ten-membered rings: the five-membered lactone ring has a twisted conformation, whereas the ten-membered ring displays an approximate chair-chair conformation. The dihedral angle between the rings is 24.76?(9)°.
| S-EPMC3011600 | biostudies-literature
Project description:THE TITLE COMPOUND, [SYSTEMATIC NAME: 5a-acet-oxy-methyl-3-isopropyl-8-methyl-1,2,3,3a,4,5,5a,6,7,10,10a,10b-dodeca-hydro-7,10-endo-epidi-oxy-cyclo-hepta-[e]indene-3a-carb-oxy-lic acid], C(22)H(32)O(6) (I), is closely related to methyl 5a-acet-oxy-methyl-3-isopropyl-8-methyl-1,2,3,3a,4,5,5a,6,7,10,10a,10b-dodeca-hydro-7,10-endo-epidi-oxy-cyclo-hepta-[e]indene-3a-carboxyl-ate, (II) [Brito et al., (2008 ▶). Acta Cryst. E64, o1209]. There are two mol-ecules in the asymmetric unit, which are linked by two strong intra-molecular O-H⋯O hydrogen bonds with graph-set motif R(2) (2)(8). In both (I) and (II), the conformation of the three fused rings are almost identical. The five-membered ring has an envelope conformation, the six-membered ring has a chair conformation and the seven-membered ring has a boat conformation. The most obvious differences between the two compounds is the observed disorder of the acet-oxy-methyl fragments in both mol-ecules of the asymmetric unit of (I). This disorder is not observed in (II). The crystal structure and the molecular conformation is stabilized by intermolecular C-H⋯O hydrogen bonds. The ability to form hydrogen bonds is different in the two compounds. The crystal studied was a non-merohedral twin, the ratio of the twin components being 0.28 (1):0.72 (1).
| S-EPMC3007890 | biostudies-literature
Project description:The title compound, C(16)H(12)O(6), is a common impurity of ortho-acetyl-salicylic acid (aspirin). The benzene rings form a dihedral angle of 81.9 (1)° while the acetyl and carboxyl groups form dihedral angles of 74.0 (1) and 26.4 (2)°, respectively, with the benzene rings to which they are bound. In the crystal, mol-ecules are linked by pairs of O-H⋯O hydrogen bonds between the carboxyl groups, forming inversion dimers.
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Project description:In the title compound, C(13)H(10)O(4), an analog of acetyl-salicylic acid, the naphthalene unit is twisted slightly due to ortho disubstitution [dihedral angle between conjugated rings system in the naphthalene unit = 2.0?(2)°]. The mean planes of the carb-oxy-lic and ester groups are almost coplanar and perpendicular, respectively, to the mean plane of the conjugated aromatic system, making dihedral angles of 8.9?(3) and 89.3?(1)°. In the crystal, mol-ecules are paired through their carb-oxy-lic groups by the typical centrosymmetric O-H?O inter-actions with R(2) (2)(8) hydrogen-bond motifs. In addition, several weak C-H?O inter-molecular contacts are also observed. Finally, the mol-ecules are stacked along crystallographic [100] and [010] directions.
| S-EPMC3009309 | biostudies-literature
Project description:In the title compound, C(19)H(18)O(5), the ester group is twisted with respect to the acetyl-salicylic acid and eugenol rings at dihedral angles of 22.48?(2) and 81.07?(1)°, respectively. The dihedral angle between the two benzene rings is 60.72?(1)°. The crystal packing exhibits no significantly short inter-molecular contacts.
| S-EPMC3152028 | biostudies-literature
Project description:The title compound, C(10)H(10)O(4), crystallizes with the well-known carb-oxy-lic acid dimer-forming R(2) (2)(8) hydrogen-bond motif. Chains approximately parallel to (-1-12) are then built through C(methyl-ene,phen-yl)-H?O(carbon-yl) inter-actions [C(6) and C(8) motifs] with one (meth-yl)C-H?? inter-action providing inter-planar binding. The weakness of the latter inter-action is consistent with the difficulty experienced in obtaining suitable single crystals.
| S-EPMC3569790 | biostudies-literature
Project description:Four of the five six-membered rings of the title penta-cyclic triterpene, C(33)H(52)O(4), adopt chair conformations; the fifth, which has a C=C double bond, adopts an approximate envelope conformation.
| S-EPMC2969982 | biostudies-literature
Project description:BACKGROUND:Gamma valerolactone (GVL) treatment of lignocellulosic bomass is a promising technology for degradation of biomass for biofuel production; however, GVL is toxic to fermentative microbes. Using a combination of chemical genomics with the yeast (Saccharomyces cerevisiae) deletion collection to identify sensitive and resistant mutants, and chemical proteomics to monitor protein abundance in the presence of GVL, we sought to understand the mechanism toxicity and resistance to GVL with the goal of engineering a GVL-tolerant, xylose-fermenting yeast. RESULTS:Chemical genomic profiling of GVL predicted that this chemical affects membranes and membrane-bound processes. We show that GVL causes rapid, dose-dependent cell permeability, and is synergistic with ethanol. Chemical genomic profiling of GVL revealed that deletion of the functionally related enzymes Pad1p and Fdc1p, which act together to decarboxylate cinnamic acid and its derivatives to vinyl forms, increases yeast tolerance to GVL. Further, overexpression of Pad1p sensitizes cells to GVL toxicity. To improve GVL tolerance, we deleted PAD1 and FDC1 in a xylose-fermenting yeast strain. The modified strain exhibited increased anaerobic growth, sugar utilization, and ethanol production in synthetic hydrolysate with 1.5% GVL, and under other conditions. Chemical proteomic profiling of the engineered strain revealed that enzymes involved in ergosterol biosynthesis were more abundant in the presence of GVL compared to the background strain. The engineered GVL strain contained greater amounts of ergosterol than the background strain. CONCLUSIONS:We found that GVL exerts toxicity to yeast by compromising cellular membranes, and that this toxicity is synergistic with ethanol. Deletion of PAD1 and FDC1 conferred GVL resistance to a xylose-fermenting yeast strain by increasing ergosterol accumulation in aerobically grown cells. The GVL-tolerant strain fermented sugars in the presence of GVL levels that were inhibitory to the unmodified strain. This strain represents a xylose fermenting yeast specifically tailored to GVL produced hydrolysates.
| S-EPMC5767017 | biostudies-literature
Project description:Two independent mol-ecules comprise the asymmetric unit of the title cholestane derivative, C(29)H(49)NO(3) {systematic name: (3S,8S,9S,10R,13R,14S,17R)-17-[(1R)-1,5-dimethyl-hex-yl]-6-hy-droxy-imino-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetra-deca-hydro-1H-cyclo-penta-[a]phenanthren-3-yl ace-tate}. The major differences between the mol-ecules relate to the relative orientations of the terminal acetyl [C-C-O-C torsion angles = -158.8?(3) and -81.7?(3)°] and alkyl groups [C-C-C-C = 168.9?(3) and 65.8?(4)°]. In the crystal, the independent mol-ecules associate via pairs of O-H?N hydrogen bonds, forming dimeric aggregates. Supra-molecular layers in the ab plane are mediated by C-H?O inter-actions.
| S-EPMC3100065 | biostudies-literature