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[ CAS No. 531-95-3 ]

{[proInfo.proName]} (Synonyms:(S)-Equol; (-)-(S)-Equol) ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 531-95-3
Chemical Structure| 531-95-3
Structure of 531-95-3 * Storage: {[proInfo.prStorage]}

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Product Details of [ 531-95-3 ]

CAS No. :531-95-3 MDL No. :MFCD00200962
Formula : C15H14O3 Boiling Point : 441.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :242.27 g/mol Pubchem ID :91469
Synonyms :

1. Equol

Safety of [ 531-95-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 531-95-3 ]

  • Upstream synthesis route of [ 531-95-3 ]
  • Downstream synthetic route of [ 531-95-3 ]

[ 531-95-3 ] Synthesis Path-Upstream   1~45

  • 1
  • [ 922179-56-4 ]
  • [ 531-95-3 ]
YieldReaction ConditionsOperation in experiment
93% With hydrogenchloride; methanol In dichloromethane at 4.8 - 20℃; for 6 h; Example 6; Deprotecting the bis-MOM-S-equol to S-Equol ((S)-3-(4-hydroxyphenyl)-chroman-7-ol); A solution of 42.17 g (0.128 mol) of (S)-bis-MOM-equol in 200 mL of 1:1 mixture of CH2Cl2/MeOH was placed in a 1 L 3-neck round bottom flask equipped with a magnetic stirrer, thermocouple, cooling ice bath and nitrogen line. A total of 200 mL of 10 wt percent solution of HCl in MeOH (0.438 mol, 3.4 eq.) was slowly added to pre-chilled (4.8° C.) solution of bis-MOM-equol. The reaction mixture was allowed to warm up to room temperature and monitored by TLC until all starting material is converted to S-equol (Rf=0.58 for bis-MOM-equol, 0.28 for mono-MOM-equol, and 0.10 for S-equol in ethyl acetate/hexane=2:8). After 6 hours at room temperature a complete deprotection was observed. Solvent was removed under reduced pressure and precipitated solid was treated with a 500 mL of ice-cold water, extracted with ethyl acetate (2.x.400 mL) and combined organic phases were washed with diluted sodium bicarbonate (400 mL). Organic layer was dried over sodium sulfate and solvent volume was reduced to about 100 mL. The obtained yellowish solution was carefully diluted with 400 mL of hexane and resulted clear solution was chilled on an ice bath while stirring. Precipitated white solid was filtered off, washed with hexane (3.x.200 mL) and dried in a vacuum oven overnight to yield 25.24 g of s-equol as a white solid. An additional 3.54 g of the product was obtained from mother liquor. A total 28.78 g (93percent isolated yield) of S-equol was obtained as a white solid with mp 162 C. Chemical HPLC and optical purity for synthesized S-equol were found to be 96.69percent and 100percent ee correspondingly. Reversed Phase HPLC used to determine chemical purity: Column: Waters Symmetry C18, 3.5 micron particles, 4.6.x.75 mm Mobile phase A: 0.1percent TFA in water Mobile phase B: 0.1percent TFA in acetonitrile Gradient: 5percent B to 100percent B in 16 minutes, return to initial conditions at 16 minutes. Detector wavelength=280 nm Injection volume=5 microliters Retention time: 7.87 min HPLC purity: 96.69percent Optical purity was determine by chiral HPLC: Column: Chiracel OJ, 4.6.x.250 mm Isocratic, 75percent (0.2percent phosphoric acid in water), 25percent acetonitrile Flow: 0.75 mL/min Detector wavelength: 215 nm Retention time: 54.28 min Chiral purity: 100percent ee Optical rotation: [α]=-19.1° C. A reported optical rotation for S-equol crystallized from aqueous ethanol is [α]=-21.5° C. (The Merck Index, 1996, 12th edition, p 618). LC-MS traces and spectra of the S-Equol product are shown in FIGS. 6A and 6B, respectively. 1H NMR and 13C NMR data appear below. 1H NMR (300 MHz, CDCl3, δ): 9.32 (s, 1H, OH), 9.21 (s, 1H, OH), 7.09 (d, 2H, J=8.4 Hz), 6.86 (d, 1H, J=8.1 Hz), 6.72 (d, 2H, J=8.7 Hz), 6.30 (dd, 1H, J=8.4 J=2.1), 6.21 (d, 1H, J=2.4 Hz), 4.15 (ddd, 1H, CH2O, J=10.5 Hz, J=1.80 Hz), 3.88 (t, 1H, CH2O, J=10.2 Hz), 3.00 (m, 1H, CH), 2.78 (m, 2H, CH2). 13C NMR (75 MHz, CDCl3, δ): 156.515 (C7), 156.151 (C4'), 154.557 (C9), 131.711 (C10), 130.134 (C8), 128.346 (C6), 115.321 (C3'), 112.627 (C1'), 108.048 (C5), 102.547 (C2'), 70.309 (C2), 37.197 (C3), 31.324 (C4).
Reference: [1] Patent: US2007/27329, 2007, A1, . Location in patent: Page/Page column 10-11
[2] Organic Letters, 2018, vol. 20, # 10, p. 3006 - 3009
  • 2
  • [ 1383121-33-2 ]
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YieldReaction ConditionsOperation in experiment
91% With potassium carbonate In acetone at 50℃; for 8 h; A mixture of phenol 6 (259 mg, 0.8 mmol) and K2CO3 (536 mg, 3.88 mmol) in 12 mL acetone was stirred at 50 °C for 8 h, cooled to room temperature, and filtered through a pad of Celite. The filtrate was concentrated and the residue was purified by chromatography on silica gel (PE/EA=3:1) to afford (S)-equol (177 mg, 91percent yield) as a white solid. 97percent ee, -13.9 (c 0.21, EtOH), HPLC condition: Chiralpak AD-H column (25.x.0.46 cm ID), n-hexane/2-propanol=80:20, 1.0 mL/min, 254 nm UV detector, tR=5.24 min for (R)-enantiomer and tR=7.22 min for (S)-enantiomer. Mp 190-191 °C. 1H NMR (400 MHz, DMSO-d6) δ 9.30 (s, 1H, OH), 9.19 (s, 1H, OH), 7.10 (d, J=8.4 Hz, 2H, Ar-H), 6.86 (d, J=8.0 Hz, 1H, Ar-H), 6.72 (d, J=8.4 Hz, 2H, Ar-H), 6.29 (dd, J=8.0 and 2.0 Hz, 1H, Ar-H), 6.19 (d, J=1.6 Hz, 1H, Ar-H), 4.14 (d, J=8.0 Hz, 1H, CH2), 3.89 (t, J=10.4 Hz, 1H, CH2), 3.04-2.97 (m, 1H, CH), 2.86-2.73 (m, 2H, CH2). 13C NMR (100 MHz, DMSO-d6) δ 156.5, 156.1, 154.5, 131.7, 130.1, 128.3, 115.3, 112.6, 108.0, 102.6, 70.3, 37.2, 31.3. HRMS (ESI) calcd for [M-H, C15H13O3]-: 241.0870, found 241.0869.
Reference: [1] Tetrahedron, 2012, vol. 68, # 26, p. 5172 - 5178
[2] Tetrahedron, 2010, vol. 66, # 1, p. 197 - 207
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YieldReaction ConditionsOperation in experiment
88% at 150℃; Inert atmosphere The dimethoxy chromane (−)-23 (18g, 66.7mmol) was dissolved in pyridine hydrochloride (192g, 148mL, 1.67mol), heated overnight at 150°C and cooled to room temperature. After neutralizing with excessive NaHCO3 (aqueous), the mixture was extracted with dichloromethane (3×100mL). The crude product was further purified by column chromatography using diethyl ether in hexanes to yield white solid in 88percent yield. (14.2g, 58.7mmol). 3.8.1 (S)-3-(4-Hydroxyphenyl)chroman-7-ol. (S)-(−)-Equol (−)-4 [α]25D [α]D25 =−19.5 (c=1.05, MeOH), lit46 [α]25D [α]D25 =−13 (c=0.21, EtOH); 1H NMR (400MHz, CD3OD) δ 7.09 (d, J=8.5Hz, 2H), 6.88 (d, J=8.2Hz, 1H), 6.76 (d, J=8.5Hz, 2H), 6.33 (dd, J=8.2, 2.5Hz, 1H), 6.25 (d, J=2.5Hz, 1H), 4.20 (ddd, J=10.5, 3.6, 1.8Hz, 1H), 3.91 (t, J=10.5Hz, 1H), 3.05 (tdd, J=10.2, 6.0, 3.6Hz, 1H), 2.93–2.77 (m, 2H).·13C NMR (100MHz, CD3OD) δ 157.6, 157.3, 156.3, 133.8, 131.2, 129.3 (2C), 116.4 (2C), 114.6, 109.1, 103.8, 72.2, 39.4, 33.0.
Reference: [1] Tetrahedron, 2018, vol. 74, # 16, p. 2020 - 2029
[2] Organic Letters, 2017, vol. 19, # 18, p. 4884 - 4887
[3] Organic Letters, 2006, vol. 8, # 24, p. 5441 - 5443
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YieldReaction ConditionsOperation in experiment
95%
Stage #1: With lithium aluminium tetrahydride In diethyl ether for 3 h;
Stage #2: With water In diethyl etherCooling with ice
To a suspension Of LiAlH4 in ether, compound (4) dissolved in ether is added dropwise and stirred under backflow for about 3 hours. The reaction flask is cooled with ice water, and ice water is added carefully dropwise to the reaction mixture, until the development of hydrogen terminates. Subsequently, 10percent sulphuric acid is added until the aluminium hydroxide precipitate is dissolved. The organic phase is removed in a separatory funnel and purified by flash chromatography at a silica-gel (230-400 mesh) with the eluants ethylacetate/hexane(4: 1 v/v). The enantiomeric purity of the product is determined by HPLC at a chiral acid as 98percent ee (25 cm Chiralcel OD-H chiral column; A ethanol/hexane 10/90; B ethanol/hexane 90/10; gradient 15 min; flow rate: 1 ml/min; detection: 254 nm), yield: 95percent (S)-equol.
Reference: [1] Patent: WO2010/18199, 2010, A1, . Location in patent: Page/Page column 11
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Reference: [1] Bioscience, Biotechnology and Biochemistry, 2008, vol. 72, # 10, p. 2660 - 2666
[2] Chemical and Pharmaceutical Bulletin, 2009, vol. 57, # 4, p. 346 - 360
  • 6
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YieldReaction ConditionsOperation in experiment
36 g With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 15 - 20℃; To a mixture of alcohol of formula (9) (50 g) and triphenyl phosphine (151 g) in THF (2.5 L) diisopropyl azodicarboxylate (1 16.5 g) in THF (500 mL) was added at 15-20 °C and maintained at that temperature for 1 -2 hours. About 5percent lithium hydroxide solution (1000 mL) was added into the reaction mass and extracted with MTBE (3 x 750 mL) to remove the organic impurities. The pH of the aqueous layer was adjusted to 1 -4 by dilute hydrochloric acid (250 mL). The reaction mass was maintained at RT for 5-6 hours and the product was filtered off. The crude product was taken with I PA (7.5 vol) and added water (22.5 vol). The reaction mass was then maintained at RT for 12-14 hours. The solid was filtered and dried at 50-55 for 10-12 hours to afford the title compound. Yield: 36 g Chemical purity (by HPLC): 98.9percent. Chiral purity (by HPLC): 99.7percent e.e. 1 H NMR (400 MHz, DMSO- d6) δ: 2.50-2.87 (m, 2H), 2.97-3.34 (m, 1 H), 3.86-3.92 (m, 1 H), 4.13-4.16 (m, 1 H), 6.18 (d, J=2.4 Hz, 1 H) , 6.27-6.29 (dd, J=8.0 Hz, J=2.0 Hz, 1 H), 6.71 (d, J=8.8 Hz, 2H), 6.86 (d, J=7.6 Hz, 1 H), 7.10 (d, J=8.4 Hz, 2H), 9.14 (s, 1 H), 9.26 (s, 1 H). MS: m/z = 243.10 [M+1 ].
36 g With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 15 - 20℃; To a mixture of alcohol of formula (9) (50 g) and triphenyl phosphine (151 g) in THF (2.5 L) diisopropyl azodicarboxylate (116.5 g) in THF (500 mL) was added at 15-20° C. and maintained at that temperature for 1-2 hours.
About 5percent lithium hydroxide solution (1000 mL) was added into the reaction mass and extracted with MTBE (3*750 mL) to remove the organic impurities.
The pH of the aqueous layer was adjusted to 1-4 by dilute hydrochloric acid (250 mL).
The reaction mass was maintained at RT for 5-6 hours and the product was filtered off.
The crude product was taken with IPA (7.5 vol) and added water (22.5 vol).
The reaction mass was then maintained at RT for 12-14 hours.
The solid was filtered and dried at 50-55° C. for 10-12 hours to afford the title compound.
Yield: 36 g
Chemical purity (by HPLC): 98.9percent.
Chiral purity (by HPLC): 99.7percent e.e.
1H NMR (400 MHz, DMSO-d6) δ: 2.50-2.87 (m, 2H), 2.97-3.34 (m, 1H), 3.86-3.92 (m, 1H), 4.13-4.16 (m, 1H), 6.18 (d, J=2.4 Hz, 1H), 6.27-6.29 (dd, J=8.0 Hz, J=2.0 Hz, 1H), 6.71 (d, J=8.8 Hz, 2H), 6.86 (d, J=7.6 Hz, 1H), 7.10 (d, J=8.4 Hz, 2H), 9.14 (s, 1H), 9.26 (s, 1H).
MS: m/z=243.10 [M+1].
Reference: [1] Patent: WO2013/144857, 2013, A1, . Location in patent: Page/Page column 22; 23
[2] Patent: US2015/57456, 2015, A1, . Location in patent: Paragraph 0074-0079
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Reference: [1] Organic Letters, 2006, vol. 8, # 24, p. 5441 - 5443
[2] Tetrahedron, 2012, vol. 68, # 26, p. 5172 - 5178
[3] Journal of the American Chemical Society, 2012, vol. 134, # 44, p. 18245 - 18248
[4] Tetrahedron, 2018, vol. 74, # 16, p. 2020 - 2029
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Reference: [1] Organic Letters, 2006, vol. 8, # 24, p. 5441 - 5443
[2] Journal of the American Chemical Society, 2012, vol. 134, # 44, p. 18245 - 18248
[3] Tetrahedron, 2018, vol. 74, # 16, p. 2020 - 2029
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Reference: [1] Bioscience, Biotechnology and Biochemistry, 2008, vol. 72, # 10, p. 2660 - 2666
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Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 6, p. 1559 - 1567
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Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 44, p. 18245 - 18248
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Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 6, p. 1559 - 1567
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Reference: [1] Organic Letters, 2006, vol. 8, # 24, p. 5441 - 5443
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Reference: [1] Organic Letters, 2006, vol. 8, # 24, p. 5441 - 5443
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Reference: [1] Organic Letters, 2006, vol. 8, # 24, p. 5441 - 5443
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Reference: [1] Organic Letters, 2017, vol. 19, # 18, p. 4884 - 4887
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Reference: [1] Organic Letters, 2017, vol. 19, # 18, p. 4884 - 4887
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Reference: [1] Organic Letters, 2017, vol. 19, # 18, p. 4884 - 4887
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Reference: [1] Organic Letters, 2018, vol. 20, # 10, p. 3006 - 3009
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  • [ 486-66-8 ]
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Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 6, p. 1559 - 1567
[2] Patent: JP2015/44770, 2015, A,
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Reference: [1] Chemical and Pharmaceutical Bulletin, 2009, vol. 57, # 4, p. 346 - 360
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Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 44, p. 18245 - 18248
[2] Tetrahedron, 2018, vol. 74, # 16, p. 2020 - 2029
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Reference: [1] Tetrahedron, 2012, vol. 68, # 26, p. 5172 - 5178
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Reference: [1] Tetrahedron, 2012, vol. 68, # 26, p. 5172 - 5178
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Reference: [1] Tetrahedron, 2012, vol. 68, # 26, p. 5172 - 5178
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Reference: [1] Tetrahedron, 2012, vol. 68, # 26, p. 5172 - 5178
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Reference: [1] Tetrahedron, 2012, vol. 68, # 26, p. 5172 - 5178
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Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 44, p. 18245 - 18248
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Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 44, p. 18245 - 18248
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Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 44, p. 18245 - 18248
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Reference: [1] Patent: US2015/57456, 2015, A1,
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Reference: [1] Patent: US2015/57456, 2015, A1,
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Reference: [1] Patent: US2015/57456, 2015, A1,
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Reference: [1] Patent: US2015/57456, 2015, A1,
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Reference: [1] Patent: US2015/57456, 2015, A1,
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Reference: [1] Patent: US2015/57456, 2015, A1,
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Reference: [1] Chemical Communications, 2015, vol. 51, # 32, p. 7012 - 7014
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Reference: [1] Chemical Communications, 2015, vol. 51, # 32, p. 7012 - 7014
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Reference: [1] Chemical Communications, 2015, vol. 51, # 32, p. 7012 - 7014
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Reference: [1] Chemical Communications, 2015, vol. 51, # 32, p. 7012 - 7014
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Reference: [1] Tetrahedron, 2018, vol. 74, # 16, p. 2020 - 2029
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Reference: [1] Tetrahedron, 2018, vol. 74, # 16, p. 2020 - 2029
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Reference: [1] Tetrahedron, 2018, vol. 74, # 16, p. 2020 - 2029
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Reference: [1] Patent: JP2015/44770, 2015, A,
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Reference: [1] Chemische Berichte, 1939, vol. 72, p. 629,632
Historical Records

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[ 531-95-3 ]

Chemical Structure| 221054-79-1

A620368[ 221054-79-1 ]

(R)-3-(4-Hydroxyphenyl)chroman-7-ol

Reason: Optical isomers