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[ CAS No. 60-12-8 ] {[proInfo.proName]}

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Chemical Structure| 60-12-8
Chemical Structure| 60-12-8
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Product Citations

Product Citations      Expand+

Anushree Mondal ; Pronay Roy ; Jaclyn Carrannatto , et al. DOI: PubMed ID:

Abstract: The prenylated-flavin mononucleotide-dependent decarboxylases (also known as UbiD-like enzymes) are the most recently discovered family of decarboxylases. The modified flavin facilitates the decarboxylation of unsaturated carboxylic acids through a novel mechanism involving 1,3-dipolar cyclo-addition chemistry. UbiD-like enzymes have attracted considerable interest for biocatalysis applications due to their ability to catalyse (de)carboxylation reactions on a broad range of aromatic substrates at otherwise unreactive carbon centres. There are now ～35[thin space (1/6-em)]000 protein sequences annotated as hypothetical UbiD-like enzymes. Sequence similarity network analyses of the UbiD protein family suggests that there are likely dozens of distinct decarboxylase enzymes represented within this family. Furthermore, many of the enzymes so far characterized can decarboxylate a broad range of substrates. Here we describe a strategy to identify potential substrates of UbiD-like enzymes based on detecting enzyme-catalysed solvent deuterium exchange into potential substrates. Using ferulic acid decarboxylase (FDC) as a model system, we tested a diverse range of aromatic and heterocyclic molecules for their ability to undergo enzyme-catalysed H/D exchange in deuterated buffer. We found that FDC catalyses H/D exchange, albeit at generally very low levels, into a wide range of small, aromatic molecules that have little resemblance to its physiological substrate. In contrast, the sub-set of aromatic carboxylic acids that are substrates for FDC-catalysed decarboxylation is much smaller. We discuss the implications of these findings for screening uncharacterized UbiD-like enzymes for novel (de)carboxylase activity.

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ;

Chufan Andrew Jin ; DOI:

Abstract: Reactive species that are employed as electrophiles in functionalization of substrates are typically prepared from native functionality such as alcohols and carboxylic acids. The addition of a pre-functionalization step of native substrates can reduce the efficiency of syntheses. These pre-functionalization reactions along with the functionalization reactions themselves proceed through polar mechanisms, limiting the scope of both functionalization and pre-functionalization reactions. Reported herein are preliminary efforts in the development of a deoxy-functionalization protocol for secondary and tertiary alcohols. The reported protocol proceeds through a derived Barton-McCombie deoxygenation mediated by a super silyl radical. Transfer of a thiocarbonate activating group to the silyl radical generates carbon radical which can be trapped out with an external sulfonyl trap, generating sulfonyl radical, which may then react with an allylic silane allowing for turnover of the radical chain.

Purchased from AmBeed: ; ;

Valdez Castillo, Mariana ; Brar, Satinder Kaur ; Arriaga, Sonia , et al. DOI:

Abstract: Whey is one of the main residues of the dairy industry and its valorization by fermentation is an emergent practice that contributes to the circular economy and sustainable development. Whey fermentation with specialized yeast strains produces value-added biomols., such as fusel alcs. of high interest for the pharmaceutic, food and cosmetic industries due to their aromatic and flavor properties. The present study aimed to develop the whey fermentation with the yeasts Kluyveromyces marxianus and Debaryomyces hansenii immobilized on inert support, to increase cell d. and 2-phenylethanol (2-PE) production Biochar synthesized from wood feedstock, perlite and filter Kaldnes plastic rings were used as supports for the cell immobilization. They were selected based on their different nature and phys. properties such as porous structure and rough surface, to study the effect of different supports on yeast biofilm development. Also, functional groups such as hydroxyl, carbonyl, siloxane, and aliphatic hydrocarbons were useful for the development of covalent bonds and electrostatic forces between cells-support. The yeast immobilization increased the 2-PE production, especially on the plastic rings and perlite, obtaining 0.56 ± 0.01 g/L of 2-PE for the suspended culture and up to 0.91 ± 0.01 g/L for the immobilized co-culture on filter Kaldnes plastic rings.

Keywords: Whey fermentation ; Yeast immobilization ; Wood biochar ; Perlite ; Plastic rings ; 2-Phenylethanol production

Purchased from AmBeed:

Product Details of [ 60-12-8 ]

CAS No. :60-12-8 MDL No. :MFCD00002886
Formula : C8H10O Boiling Point : -
Linear Structure Formula :C6H5(CH2)2OH InChI Key :WRMNZCZEMHIOCP-UHFFFAOYSA-N
M.W : 122.16 Pubchem ID :6054
Synonyms :
Phenylethyl alcohol;Phenethyl alcohol;NSC 406252;Phenylethanol;Benzeneethanol;2-Phenylethyl alcohol;Benzyl carbinol

Calculated chemistry of [ 60-12-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 37.38
TPSA : 20.23 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.7
Log Po/w (XLOGP3) : 1.36
Log Po/w (WLOGP) : 1.22
Log Po/w (MLOGP) : 1.87
Log Po/w (SILICOS-IT) : 2.03
Consensus Log Po/w : 1.64

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.82
Solubility : 1.87 mg/ml ; 0.0153 mol/l
Class : Very soluble
Log S (Ali) : -1.39
Solubility : 5.01 mg/ml ; 0.041 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.58
Solubility : 0.318 mg/ml ; 0.0026 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 60-12-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P280-P301+P312+P330-P305+P351+P338-P312-P337+P313-P501 UN#:N/A
Hazard Statements:H302-H313-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 60-12-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 60-12-8 ]

[ 60-12-8 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 60-12-8 ]
  • [ 102-20-5 ]
YieldReaction ConditionsOperation in experiment
27% With calcium dichloride dihydrate; oxone; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; water; In dichloromethane; at 20℃; for 24h; General procedure: The respective alcohol (1.0 mmol) was added to a suspension of Oxone (400.0 mg, m., CaCl2*2H2O (73.5 mg, 0.5 mmol) and TEMPO (1.6 mg, 0.01 mmol) in dichloromethane (2 mL). The reaction was initiated by the addition of 0.1 mL DI water. The reaction mixture was stirred at RT for the indicated times or until TLC or GC/MS showed consumption of the starting material and then filtered. After evaporation of the solvent using a rotavap, the crude reaction mixtures were separated via column chromatography to yield the desired ester dimers.
  • 2
  • [ 4427-92-3 ]
  • [ 96-09-3 ]
  • [ 60-12-8 ]
  • [ 2979-22-8 ]
  • [ 122-78-1 ]
  • [ 103-29-7 ]
  • 3
  • [ 60-12-8 ]
  • [ 13827-62-8 ]
  • Naphthalene-2,6-disulfonic acid diphenethyl ester [ No CAS ]
  • 4
  • [ 60-12-8 ]
  • [ 331-39-5 ]
  • [ 104594-70-9 ]
  • N,N'-dicyclohexyl-O-(3,4-dihydrocinnamoyl)isourea [ No CAS ]
  • 5
  • [ 60-12-8 ]
  • [ 331-39-5 ]
  • [ 104594-70-9 ]
YieldReaction ConditionsOperation in experiment
48% With ytterbium(III) triflate; In nitromethane; at 120℃; for 0.666667h;Catalytic behavior; To a mixture of caffeic acid fine powder (1.0 g, 5.56 mmol, 1.0 equiv.),alcohol (5.56 mmol, 1.0 equiv.) in nitromethane (125 mL) was addedytterbium triflate (34.4 mg, 0.056 mmol, 0.01 equiv.). After 5 min inan ultrasonic bath the mixture without protective gas was stirred ona 120 C oil bath for a given time. The reaction mixture was cooled toroom temperature, washed with deionised water (30 mL), 2% NaHCO3(30 mL) and brine, dried over anhydrous Na2SO4 and evaporated underreduced pressure to give the crude product, which was purified on asilica gel column to give the compounds 1-5 and 8-30.2-Phenethyl (E)-3-(3,4-dihydroxyphenyl) acrylate (1): Whitesolid; yield 758 mg, 48.0%; m.p. 128-130 C (lit.20 116-123 C);IR (KBr) numax 3480, 3328, 1683, 1601, 1362, 1301, 1279, 1182 cm-1;1H NMR (400 MHz, DMSO-d6) deltaH 7.46 (1H, d, J = 16 Hz, CH=CHCO),7.34-7.18 (5H, m, C6H5), 7.05 (1H, s, 2-ArH), 6.99 (1H, d, J = 8.0 Hz,6-ArH), 6.77 (1H, d, J = 8.0 Hz, 5-ArH), 6.24 (1H, d, J = 16 Hz,CH=CHCO), 4.32 (2H, t, J = 6.8 Hz, OCH2), 2.94 (2H, t, J = 6.8 Hz,OCH2CH2) ppm; 13C NMR (100 MHz, DMSO-d6) deltaC 166.4, 148.3,145.4, 145.1, 138.0, 128.8, 128.3, 126.3, 125.4, 121.4, 115.7, 114.7, 113.8,64.3, 34.4 ppm; HRMS-ESI C17H16O4 calcd [M-H]- 283.0970, found283.0966.
48% With ytterbium(III) triflate; In nitromethane; at 120℃; General procedure: To a mixture of caffeic acid fine powder (1.0 g, 5.56 mmol), various phenethyl alcohols (5.56 mmol) in CH3NO2 (125 mL) was added Yb(OTf)3 (34.4 mg, 0.056 mmol). After 5 min of ultrasonic shake, the mixture was stirred on a 120 C oil bath for 40-120 min. The reaction mixture was cooled to room temperature, washed with 2% NaHCO3 (30 mL) and brine, dried over anhydrous Na2SO4, and concentrated to give crude products, which were purified by column chromatography to give the compounds 1-26 in 18-61% yields. Phenethyl (E)-3-(3,4-dihydroxyphenyl) acrylate (CAPE). White solid (48% yield for esterification reaction); Mp 128-130 C; 1H NMR (400 MHz, DMSO-d6) deltaH 7.46 (1H, d, J = 16.0 Hz, CH=CHCO), 7.34-7.18 (5H, m, C6H5), 7.05 (1H, s, 2-ArH), 6.99 (1H, d, J = 8.0 Hz, 5-ArH), 6.77 (1H, d, J = 8.0 Hz, 6-ArH), 6.24 (1H, d, J = 16.0 Hz, CH=CHCO), 4.32 (2H, t, J = 6.8 Hz, OCH2), 2.94 (2H, t, J = 6.8 Hz, CH2C6H5) ppm; 13C NMR (100 MHz, DMSO-d6) deltaC 166.4, 148.3, 145.4, 145.1, 138.0, 128.8, 128.3, 126.3, 125.4, 121.4, 115.7, 114.7, 113.8, 64.3, 34.4 ppm; HRMS-ESI C17H16O4 calcd [M-H]- 283.0970, found 283.0966.
9% With ytterbium(III) triflate; In nitromethane; for 1.5h;Reflux; Caffeic acid (0.5 g, 2.78 mmol) and 2-phenylethanol (0.35 mL,2.78 mmol) were dissolved in nitromethane (62.5 mL). Yb(OTf)3(0.017 g, 0.028 mmol) was added, and the suspension was stirredfor 5 min in an ultrasonic bath followed by an additional 1.5 hstirring under reflux [4]. The reaction mixture was stirred at roomtemperature overnight and washed with NaHCO3-solution (2%,15 mL) and brine (15 mL). The organic phase was dried over Na2SO4and concentrated under reduced pressure. The crude product waspurified by column chromatography (silica gel; chloroform/methanol,99:1), and compound 17 was obtained as a white solid (0.07 g,9%); RF 0.04 (silica gel; chloroform/methanol, 99:1); m.p.128-130 C (lit.: [19]: 126-128 C); IR (KBr): nu 3480s, 1685m,1636m, 1602s, 1535w, 1442w, 1363w, 1302m, 1279s, 1182s cm1;UV-vis (CHCl3): lambda (log epsilon) 250 (4.06), 320 (4.21), 353 (4.28) nm; 1HNMR (500 MHz, CDCl3): delta 7.56 (d, J 15.9 Hz, 1H, 3-H), 7.34-7.30(m, 2H, 2-H), 7.27-7.22 (m, 3H, 3-H4-H), 7.07 (d, J 2.0 Hz, 1H, 50-H), 7.01 (dd, J 8.2, 2.0 Hz, 1H, 20-H), 6.87 (d, J 8.2 Hz, 1H, 60-H),6.25 (d, J 15.9 Hz, 1H, 2-H), 4.42 (t, J 7.1 Hz, 2H, 1-H), 3.01 (t,J 7.1 Hz, 2H, 2-H); 13C NMR (125 MHz, CDCl3): delta 167.8 (C-1),146.5 (C-40), 145.2 (C-30), 143.9 (C-3), 138.0 (C-1), 129.1 (C-3), 128.7(C-2), 127.7 (C-10), 126.8 (C-4), 122.7 (C-60), 115.7 (C-2), 115.6 (C-50),144.6 (C-20), 65.3 (C-1), 35.4 (C-2) ppm; MS (ESI, MeOH): m/z(%) 285.0 ([MH], 45), 302.2 ([MNH4], 23), 307.1 ([MNa],100), 446.1 ([3 MKH]2, 44), 580.1 ([4 MNaH]2, 23), 588.0([4MKH]2, 50), 590.8 ([2MNa], 42), 599.9 ([4MZn]2, 48);analysis calcd for C17H16O4 (284.31): C 71.82, H 5.67; found: C 71.69,H 5.83.
With toluene-4-sulfonic acid; In benzene; Synthesis of Cinnamic Acid Analogues. The synthesis of cinnamic acid analogues was achieved by straight forward application of literature techniques. Two general approaches, designated "method A" and "method B" were utilized: Method A: Synthesis of Caffeic acid beta-phenylethyl ester (CAPE, 67H-42-A). A solution of 1.80 g (10.0 mmol) of caffeic acid, 17.9 mL (150 mmol) of beta-phenylethyl alcohol and 100 mg of p-toluenesulfonic acid in benzene (100 mL) were stirred overnight at reflux with a Dean Stark trap. Solvent and excess alcohol were removed by distillation and residue purified by silica gel chromatography (petroleum ether/CHCl3). Product was crystallized (ether/petroleum ether) to provide 67H-42-A as snow-white crystals, 1.0 g (35%): mp 128.0 C. 126-128 C.) (Grunberger, D. et al., Experimentia, (1988) 44:230-2).
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 48h; General procedure: Cinnamicacid esters (13-22) were synthesized according to a modified previous procedure.31) To a mixture of cinnamic acid derivatives (Ia-d, 3.0 mmol) and the appropriate alcohol (2.0 mmol)in dry tetrahydrofuran (6mL) were added triphenylphosphine (3.0 mmol) and diisopropyl azodicarboxylate (DIAD(3.0mmol). The reaction mixture was stirred for 48h at room temperature and the whole mixture was extracted with AcOEt and saturated NaHCO3 solution, and the organic extract was washed with brine.The organic layer was dried overNa2SO4 and the solvent was evaporated under reduced pressure. The residue was then purified by silica gel column chromatography (hexane:AcOEt=2:1)to give the title compound.

  • 7
  • [ 96-09-3 ]
  • [ 67-56-1 ]
  • [ 60-12-8 ]
  • [ 2979-22-8 ]
  • 8
  • [ 96-09-3 ]
  • [ 60-12-8 ]
  • [ 2979-22-8 ]
  • 9
  • [ 3471-31-6 ]
  • [ 60-12-8 ]
  • (5-methoxy-1<i>H</i>-indol-3-yl)-acetic acid phenethyl ester [ No CAS ]
  • 10
  • [ 2882-15-7 ]
  • [ 60-12-8 ]
  • [ 288854-00-2 ]
  • 12
  • [ 381-98-6 ]
  • [ 60-12-8 ]
  • [ 252061-10-2 ]
  • 13
  • [ 60-12-8 ]
  • [ 75-64-9 ]
  • [ 102-20-5 ]
  • [ 24070-10-8 ]
  • 16
  • [ 60-12-8 ]
  • [ 939-57-1 ]
  • phenylethyl o-methylcinnamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; In water; toluene; EXAMPLE 4 Phenylethyl o-methylcinnamate A solution of 324.0 g (2.00 moles) of o-methylcinnamic acid, 428.0 g (3.5 moles) of 2-phenylethanol, 10.0 g (0.058 moles) of p-toluenesulfonic acid and 1,200 ml of toluene was refluxed under a water separator. After 15 hours, the calculated amount of water had separated off. The reaction solution was washed first with water and then with saturated sodium bicarbonate solution. The combined washwater was extracted once with ether, and the ether phase was combined with the organic phase. The combined, organic phases were fractionated over a 10 cm Vigreux column. The solvents were separated off under atmospheric pressure and in a vacuum from a water pump. The Vigreux column was replaced by a column head and the product was distilled under 0.01 mm Hg (b.p. 154-155 C./0.01 mm Hg). 394.0 g of phenylethyl o-methylcinnamate of melting point 52 to 53 C. were obtained.
  • 17
  • [ 112-30-1 ]
  • [ 112-53-8 ]
  • [ 107-92-6 ]
  • [ 137-66-6 ]
  • [ 60-12-8 ]
YieldReaction ConditionsOperation in experiment
b) a mixture consisting of 9 g of decanol, 1.0 g of dodecanol added with 1% ascorbyl palmitate, butyric acid (2.0 g), phenylethyl alcohol (6.0 g) is prepared;
  • 18
  • [ 60-12-8 ]
  • [ 51843-24-4 ]
  • 3-Acetyl-5-chloro-1-phenethylindole [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With diisopropyl (E)-azodicarboxylate; triphenylphosphine; In tetrahydrofuran; (1) To a mixture of 0.58 g (3 mmol) of <strong>[51843-24-4]3-acetyl-5-chloroindole</strong>, 1.42 g (5.4 mmol) of triphenylphosphine and 0.66 g (5.4 mmol) of phenethyl alcohol in THF (12 ml) was added under ice-cooling, 1.09 g (5.4 mmol) of diisopropyl azodicarboxylate. After stirring for 3 hours at room temperature, the mixture was concentrated under reduced pressure. The obtained residue was chromatographed on silica gel (1/4 ethyl acetate/toluene as eluant) to give 0.58 g of the titled compound as an oil. Yield: 65%. NMR(CDCl3) delta: 2.38(1H, s), 3.12(2H, t, J=7.2 Hz), 4.36(2H, t, J=7.2 Hz), 6.97-7.01(2H, m), 7.20-7.30(5H, m), 7.38(1H, s), 8.38(1H, d, J=1.8 Hz).
  • 19
  • [ 60-12-8 ]
  • [ 39207-65-3 ]
  • [ 1241621-67-9 ]
  • [ 103-48-0 ]
  • 20
  • [ 60-12-8 ]
  • [ 7768-28-7 ]
  • [ 13398-94-2 ]
  • 21
  • [ 60-12-8 ]
  • [ 520-26-3 ]
  • [ 88510-08-1 ]
  • 22
  • [ 85426-79-5 ]
  • [ 60-12-8 ]
  • [ 1338789-21-1 ]
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