(1R,2R)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid - CAS 22613-99-6
Category:
Main Product
Product Name:
(1R,2R)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid
Catalog Number:
22613-99-6
Synonyms:
(1R,2R)-2-(hydroxymethyl)-1-phenylcyclopropane-1-carboxylicacid; 22613-99-6; (1R,2R)-2-(HYDROXYMETHYL)-1-PHENYLCYCLOPROPANECARBOXYLICACID; ZINC6116549; trans-2--1-phenylcyclopropanecarboxylicacid
CAS Number:
22613-99-6
Molecular Weight:
192.21
Molecular Formula:
C11H12O3
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
C1C(C1(C2=CC=CC=C2)C(=O)O)CO
InChI:
InChI=1S/C11H12O3/c12-7-9-6-11(9,10(13)14)8-4-2-1-3-5-8/h1-5,9,12H,6-7H2,(H,13,14)/t9-,11-/m0/s1
InChIKey:
PSMORJXEGALFGQ-ONGXEEELSA-N
Chemical Structure
CAS 22613-99-6 (1R,2R)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid

Reference Reading


1.Lasiojasmonates A-C, three jasmonic acid esters produced by Lasiodiplodia sp., a grapevine pathogen.
Andolfi A1, Maddau L2, Cimmino A1, Linaldeddu BT2, Basso S1, Deidda A2, Serra S2, Evidente A3. Phytochemistry. 2014 Jul;103:145-53. doi: 10.1016/j.phytochem.2014.03.016. Epub 2014 Apr 23.
In this study, a strain (BL 101) of a species of Lasiodiplodia, not yet formally described, which was isolated from declining grapevine plants showing wedge-shaped cankers, was investigated for its ability to produce in vitro bioactive secondary metabolites. From culture filtrates of this strain three jasmonic acid esters, named lasiojasmonates A-C and 16-O-acetylbotryosphaerilactones A and C were isolated together with (1R,2R)-jasmonic acid, its methyl ester, botryosphaerilactone A, (3S,4R,5R)-4-hydroxymethyl-3,5-dimethyldihydro-2-furanone and (3R,4S)-botryodiplodin. The structures of lasiojasmonates A-C were established by spectroscopic methods as (1R*,2R*,3'S*,4'R*,5'R*)-4-hydroxymethyl-3,5-dimethyldihydro-2-furanone, (1R*,2R*,3'S*,4'R*,5'R*,10'R*,12'R*,13'R*,14'S*) and (1R*,2R*,3'S*,4'R*,5'R*,10'S*,12'R*,13'R*,14'S*)-4-(4-hydroxymethyl-3,5-dimethyltetrahydro-furan-2-yloxymethyl)-3,5-dimethyldihydro-2-furanones jasmonates (1, 4 and 5).
2.Lasiolactols A and B Produced by the Grapevine Fungal Pathogen Lasiodiplodia mediterranea.
Andolfi A1, Basso S1, Giambra S2, Conigliaro G2, Piccolo SL2, Alves A3, Burruano S2. Chem Biodivers. 2016 Mar 3. doi: 10.1002/cbdv.201500104. [Epub ahead of print]
A strain of Lasiodiplodia mediterranea, a fungus associated with grapevine decline in Sicily, produced several metabolites in liquid medium. Two new dimeric γ-lactols, lasiolactols A and B (1 and 2), were characterized as (2S*,3S*,4R*,5R*,2'S*,3'S*,4'R*,5'R*)- and (2R*,3S*,4R*,5R*,2'R*,3'S*,4'R*,5'R*)-(5-(4-hydroxymethyl-3,5-dimethyl-tetrahydro-furan-2-yloxy)-2,4-dimethyl-tetrahydro-furan-3-yl]-methanols by IR, 1D- and 2D-NMR and HR-ESI-MS. Other four metabolites were identified as botryosphaeriodiplodin, (5R)-5-hydroxylasiodiplodin, (-)-(1R,2R)-jasmonic acid, (-)-(3S,4R,5R)-4-hydroxymethyl-3,5-dimethyldihydro-2-furanone (3 - 6, resp.). The absolute configuration (R) at hydroxylated secondary C-atom C(7) was also established for compound 3. The compounds 1 - 3, 5 and 6, tested for their phytotoxic activities to grapevine cv. Inzolia leaves at different concentrations (0.125, 0.25, 0.5 and 1 mg/ml), were phytotoxic and compound 5 showed the highest toxicity.
3.Synthesis and inhibitory action on HMG-CoA synthase of racemic and optically active oxetan-2-ones (beta-lactones).
Romo D1, Harrison PH, Jenkins SI, Riddoch RW, Park K, Yang HW, Zhao C, Wright GD. Bioorg Med Chem. 1998 Aug;6(8):1255-72.
A homologous series of both C3-unsubstituted and C3-methyl substituted oxetan-2-ones (beta-lactones) was investigated as potential inhibitors of yeast 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) synthase. Several reported methods for racemic beta-lactone synthesis were studied for preparation of the target series. In addition, a novel aluminum-based Lewis acid obtained by combination of Et2AlCl with (1R,2R)-2-[(diphenyl)hydroxymethyl] cyclohexan-1-ol was studied for the asymmetric [2 + 2] cycloaddition of aldehydes and trimethylsilylketene. This Lewis acid exhibited good reactivity but variable enantioselectivity (22-85% ee). In in vitro assays using both native and recombinant HMG-CoA synthase from Saccharomyces cerevisiae, oxetan-2-ones mono-substituted at C4 with linear alkyl chains gave IC50s that decreased monotonically with chain length up to 10 carbons and then rose rapidly for longer chains. The trans isomers of 3-methyl-4-alkyl-oxetan-2-ones showed a similar trend but had 1.
4.Which hydroxy? Evidence for species differences in the regioselectivity of glucuronidation in rat, dog, and human in vitro systems and dog in vivo.
Martin IJ1, Lewis RJ, Bernstein MA, Beattie IG, Martin CA, Riley RJ, Springthorpe B. Drug Metab Dispos. 2006 Sep;34(9):1502-7. Epub 2006 Jun 8.
The glucuronidation of (1S,2R,3R,5R)-3-(hydroxymethyl)-5-[7-{[(1R,2S)-2-phenylcyclopropyl]amino}-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]cyclopentane-1,2-diol (AZ11939714) was studied in UDP-glucuronic acid (UDPGA)-supplemented hepatic microsomes from rat, dog, and human liver. The major biliary metabolite of this compound after intraduodenal administration to a beagle dog was also studied. The techniques of HPLC, HPLC-MS and HPLC-NMR were used to characterize the glucuronides. An analysis of the proton NMR chemical shift differences between parent and metabolites was sufficient to deduce the sites of glucuronidation, although these were confirmed by 2D ROESY experiments. In dog microsomes, AZ11939714 was O-glucuronidated exclusively at the 1-position of the cyclopentanediol. This glucuronide was also the major metabolite in dog bile. In human microsomes, AZ11939714 was O-glucuronidated almost exclusively at the 3-hydroxymethyl position.