512-16-3 Usage
Originator
Hebucol,Logeais,France,1957
Definition
ChEBI: A hydroxy monocarboxylic acid in which the hydroxy group is geminal to a 1-carboxypropyl group on a cyclohexane ring.
Manufacturing Process
Into a balloon flask with two lateral necks furnished with an efficient
mechanical agitator and protected from moisture by a calcium chloride guard,
there are introduced 12 g (0.185 mol) of pure powdered zinc and 20 ml of a
solution of 16.6 g (0.17 mol) of anhydrous cyclohexanone and 31.5 g (0.16
mol) of ethyl α-bromobutyrate in 25 ml of anhydrous benzene. With vigorous
stirring in a manner to put the zinc into suspension, the balloon flask is
gradually heated in an oil bath to 100°C to 105°C. After a few minutes, a
reaction starts, causing violent boiling which is maintained while adding the
balance of the reactants. Boiling is then continued for one hour. After cooling,
the reaction mixture is turned into a beaker containing 30 ml of sulfuric acid
to half (by volume) with ice. After agitation, the mixture is decanted into a
container for separation. The aqueous phase is reextracted with benzene. The
pooled benzene solutions are washed with dilute (10%) cold sulfuric acid, then
with cold sodium carbonate (5%) and then with ice water, and dried over
anhydrous sodium sulfate. The benzene is evaporated and the ester, which is
ethyl α(hydroxy-1-cyclohexyl) butyrate, is distilled off under reduced pressure.
The yield obtained was 17 to 19 g or 49% to 55%.The ester was saponified with baryta in aqueous methanol as follows:21.5 g (0.1 mol) of the above ethyl ester is saponified by boiling under reflux
for 4 hours, while agitating, with 30 g (0.095 mol) of barium oxide hydrated
to 8H2O in 250 ml of a mixture of equal volumes of methanol and water. After
concentration to one-half its volume under reduced pressure and filtration, the
aqueous solution is washed with ether and then acidified at 0°C with 10%
hydrochloric acid. The acid liberated in oily form is extracted with ether. The
ether is washed with water, dried and evaporated. The yield is 75-80% (14-15
g of crude acid) which crystallizes spontaneously little by little. It can be
crystallized in a mixture of ether and petroleum ether (1:10) or, with better
yield, in light gasoline or oil (solubility of the pure acid ranges from 0.3% at
0°C to 100% at the boiling point). The yield of crystals is 75-80%. The
α(hydroxy-1-cyclohexyl) butyric acid thus obtained is a colorless crystalline
product with a melting point of 81°C to 82°C.
Therapeutic Function
Choleretic
Check Digit Verification of cas no
The CAS Registry Mumber 512-16-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 2 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 512-16:
(5*5)+(4*1)+(3*2)+(2*1)+(1*6)=43
43 % 10 = 3
So 512-16-3 is a valid CAS Registry Number.
InChI:InChI=1/C10H18O3/c1-2-8(9(11)12)10(13)6-4-3-5-7-10/h8,13H,2-7H2,1H3,(H,11,12)
512-16-3Relevant articles and documents
Synthesis and biological evaluation of cycloalkylidene carboxylic acids as novel effectors of Ras/Raf interaction
Friese, Anke,Hell-Momeni, Katja,Zündorf, Ilse,Winckler, Thomas,Dingermann, Theodor,Dannhardt, Gerd
, p. 1535 - 1542 (2007/10/03)
The protooncogenes Ras and Raf play important roles in signal transduction pathways regulated by mitogen-activated protein kinases. Mutations of Ras that arrest the protein in its active state are frequently implicated in tumor formation. We used Ras and Raf proteins in the yeast two-hybrid system to search for natural or synthesized substances capable of modulating Ras/Raf interaction by specifically binding to one of the interacting partners. We found that cycloalkylidene carboxylic acids enhanced Ras/Raf interaction by acting on the cysteine-rich domain of Raf. Several analogues of the active substance 2-cyclohexylidene propanoic acid were synthesized and the importance of the semicyclic double bond in the stabilization of Ras/Raf interaction was demonstrated. Variation of the size and the substituents of the cyclic system as well as the length of the carboxylic acid resulted in enhanced Ras/Raf interaction.
A NOVEL SYNTHESIS OF MONO- AND DISUBSTITUTED (1-CYCLOALKENYL) ACETIC ACID DERIVATIVES VIA IONIZATION/ELIMINATION OF β-LACTONES
Black, T. Howard,Eisenbeis, Shane
, p. 2243 - 2248 (2007/10/02)
Spiro β-lactones undergo an ionization/elimination reaction to afford cycloalkenyl acetic acid derivatives in high yield and isomeric purity.
