[ CAS No. 501-98-4 ] {[proInfo.proName]}

Name: 501-98-4|Trans-4-Hydroxycinnamic Acid|95%
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SKU: A192873
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Quality Control of [ 501-98-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 501-98-4 ]

SDS Specification

Alternatived Products of [ 501-98-4 ]

Product Details of [ 501-98-4 ]

CAS No. :	501-98-4	MDL No. :	MFCD00004399
Formula :	C₉H₈O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	164.16	Pubchem ID :	-
Synonyms :	trans-4-Hydroxycinnamic acid;4-Coumaric Acid;trans-para-hydroxy Cinnamic Acid;trans-p-hydroxy Cinnamic Acid;para-hydroxy Cinnamic Acid;trans-para-Coumaric Acid;para-Coumaric Acid;Trans-p-Coumaric acid;P-Hydroxycinnamic acid;4-Hydroxycinnamic acid

Calculated chemistry of [ 501-98-4 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	45.13
TPSA :	57.53 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.95
Log Po/w (XLOGP3) :	1.46
Log Po/w (WLOGP) :	1.38
Log Po/w (MLOGP) :	1.28
Log Po/w (SILICOS-IT) :	1.22
Consensus Log Po/w :	1.26

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.02
Solubility :	1.58 mg/ml ; 0.00965 mol/l
Class :	Soluble
Log S (Ali) :	-2.27
Solubility :	0.873 mg/ml ; 0.00532 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.28
Solubility :	8.67 mg/ml ; 0.0528 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.61

Safety of [ 501-98-4 ]

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 [ 501-98-4 ]

* 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 [ 501-98-4 ]

[ 501-98-4 ] Synthesis Path-Downstream 1~88

1
[ 7400-08-0 ]
[ 501-98-4 ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,1998,vol. 62,p. 2133 - 2137
[2]Chemische Berichte,1913,vol. 46,p. 267
[3]Journal of Agricultural and Food Chemistry,2001,vol. 49,p. 177 - 182
[4]Langmuir,2010,vol. 26,p. 5405 - 5411
[5]Organic Letters,2010,vol. 12,p. 4808 - 4811
[6]Soft Matter,2011,vol. 7,p. 10713 - 10719
[7]Journal of Photochemistry and Photobiology A: Chemistry,2013,vol. 270,p. 43 - 52
[8]Journal of Agricultural and Food Chemistry,2016,vol. 64,p. 4584 - 4598

2
[ 25561-30-2 ]
[ 501-98-4 ]
Z-p-CA(TMS) [ No CAS ]

Reference： [1]Phytochemistry,1987,vol. 26,p. 1915 - 1916

3
[ 501-98-4 ]
[ 123-07-9 ]

Reference： [1]Canadian Journal of Chemistry,1983,vol. 61,p. 652 - 657
[2]Canadian Journal of Chemistry,1983,vol. 61,p. 652 - 657

4
[ 29588-94-1 ]
[ 136918-14-4 ]
[ 501-98-4 ]
[ 7400-08-0 ]
(S)-4-(4-Hydroxy-phenyl)-1,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[c]azepine-3-carboxylic acid [ No CAS ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 701 - 714

5
2-acetonyl-8-(6-O-coumaroyl-β-D-glucopyranosyl)-7-hydroxy-5-methylchromone [ No CAS ]
[ 40738-40-7 ]
[ 501-98-4 ]
[ 7400-08-0 ]
[ 104871-04-7 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 704 - 708

6
(Z)-3-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-acrylic acid methyl ester [ No CAS ]
[ 501-98-4 ]

Reference： [1]Journal of the American Chemical Society,1993,vol. 115,p. 7103 - 7110

7
7-Coumaroyloxy-14,15-epoxythapsan-14-ol [ No CAS ]
[ 501-98-4 ]
[ 92122-86-6 ]

Reference： [1]Phytochemistry,1986,vol. 25,p. 703 - 710
[2]Phytochemistry,1986,vol. 25,p. 703 - 710

8
kaempferol 3-(4"-cis-p-coumaroyl)robinobioside [ No CAS ]
[ 501-98-4 ]
kaempferol 3-O-(6''-O-β-L-rhamnopyranosyl)-β-D-galactopyranoside [ No CAS ]

Reference： [1]Phytochemistry,1987,vol. 26,p. 3331 - 3334

9
quercetin 3-(4"-cis-p-coumaroyl)robinobioside [ No CAS ]
[ 501-98-4 ]
quercetin 3-O-(6''-O-β-L-rhamnopyranosyl)-β-D-galactopyranoside [ No CAS ]

Reference： [1]Phytochemistry,1987,vol. 26,p. 3331 - 3334

10
variabiloside D [ No CAS ]
[ 501-98-4 ]
kaempferol 3-rhamnosyl (1-> 6)galactoside-7-glucoside [ No CAS ]

Reference： [1]Phytochemistry,1987,vol. 26,p. 3331 - 3334

11
variabiloside B [ No CAS ]
[ 501-98-4 ]
quercetin 3-rhamnosyl (1-> 6)galactoside-7-glucoside [ No CAS ]

Reference： [1]Phytochemistry,1987,vol. 26,p. 3331 - 3334

12
(1R,3aS,5aS,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-5a-[(E)-3-(4-hydroxy-phenyl)-acryloyloxymethyl]-1-isopropenyl-5b,8,8,11a-tetramethyl-icosahydro-cyclopenta[a]chrysene-3a-carboxylic acid [ No CAS ]
[ 501-98-4 ]
[ 7400-08-0 ]
(+)-cylicodiscic acid [ No CAS ]

Reference： [1]Phytochemistry,1998,vol. 47,p. 1367 - 1374

13
[ 6066-82-6 ]
[ 501-98-4 ]
[ 672341-24-1 ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,1998,vol. 62,p. 2133 - 2137
[2]Organic and biomolecular chemistry,2003,vol. 1,p. 3186 - 3192

14
[ 501-98-4 ]
cis-p-coumaroyl-D-arginine methyl ester [ No CAS ]

Reference： [1]Organic and biomolecular chemistry,2003,vol. 1,p. 3186 - 3192

15
[ 501-98-4 ]
[ 632323-92-3 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 2953 - 2956

16
[ 501-98-4 ]
N-[2-(7-amino-4-methylcoumarin-3-acetyl)amino]ethoxyethyl} N_α-cis-p-coumaroyl-D-arginine amide [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 2953 - 2956

17
[ 501-98-4 ]
N-{2-[(fluorescein-4-isothiocyanato)amino]ethoxyethyl} N_α-cis-p-coumaroyl-D-arginine amide [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 2953 - 2956

18
[ 501-98-4 ]
cis-p-coumaroylagmatine [ No CAS ]

Reference： [1]Bioscience, Biotechnology and Biochemistry,1998,vol. 62,p. 2133 - 2137

19
variabiloside D [ No CAS ]
[ 501-98-4 ]

Reference： [1]Phytochemistry,1987,vol. 26,p. 3331 - 3334

20
variabiloside B [ No CAS ]
[ 501-98-4 ]

Reference： [1]Phytochemistry,1987,vol. 26,p. 3331 - 3334

21
[ 3943-97-3 ]
[ 501-98-4 ]

Reference： [1]Journal of the American Chemical Society,1993,vol. 115,p. 7103 - 7110

22
[ 112-20-9 ]
[ 501-98-4 ]
(E)-3-(4-hydroxyphenyl)-N-nonylacrylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 0 - 20℃; for 1.66667h;	4-Hydroxycinnamic acid (0.500 g, 3.05 mmol) was dissolved in THF (15 mL). While cooling on ice, EDCI (1.46 g, 7.63 mmol) and HOBt (0.467 g, 3.05 mmol) were added, and the mixture was stirred for 10 minutes at the same temperature. Then, n-nonylamine (1.68 mL, 9.15 mmol) was added, and the mixture was stirred for 1.5 hours at room temperature. The reaction solution was added with water and 1 mol/L hydrochloric acid, and extracted with ethyl acetate. After the organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and then saturated brine, the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate = 2/1?1/1), and (E)-3-(4-hydroxyphenyl)-N-nonylacrylamide (0.801 g, 91% yield) was obtained. APCI-MS m/z: [M+H]+ 290.1H-NMR (DMSO-d6) delta (ppm): 0.85 (t, J = 6.6 Hz, 3H), 1.25 (m, 12H), 1.43 (m, 2H), 3.13 (m, 2H), 6.39 (d, J = 15.7 Hz, 1H), 6.78 (d, J = 8.6 Hz, 2H), 7.29 (d, J = 15.7 Hz, 1H), 7.37 (d, J = 8.6 Hz, 2H), 7.92 (t, J = 5.6 Hz, 1H), 9.80 (brs, 1H).

Reference： [1]Patent: EP1431280,2004,A1 .Location in patent: Page 23-24

23
[ 1225064-68-5 ]
[ 501-98-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 1882 - 1890

24
O-(trans-p-coumaroyl)malic acid [ No CAS ]
[ 501-98-4 ]
[ 7400-08-0 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2009,vol. 57,p. 5843 - 5852

25
[ 1899-30-5 ]
[ 501-98-4 ]
[ 7400-08-0 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2009,vol. 57,p. 5843 - 5852

26
[ 117405-49-9 ]
[ 50-99-7 ]
[ 501-98-4 ]
[ 7400-08-0 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2009,vol. 57,p. 5843 - 5852

27
[ 87099-71-6 ]
[ 501-98-4 ]
[ 7400-08-0 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2009,vol. 57,p. 5843 - 5852

28
[ 1108200-72-1 ]
[ 501-98-4 ]
[ 7400-08-0 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2009,vol. 57,p. 5843 - 5852

29
(Z)-4-coumaric acid 4-O-β-D-glucopyranoside [ No CAS ]
[ 50-99-7 ]
[ 501-98-4 ]
[ 7400-08-0 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2009,vol. 57,p. 5843 - 5852

30
3-O-(cis-p-coumaroyl)quinic acid [ No CAS ]
[ 501-98-4 ]
[ 7400-08-0 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2009,vol. 57,p. 5843 - 5852

31
[ 501-98-4 ]
[ 929713-60-0 ]

Reference： [1]Patent: WO2012/11125,2012,A1

32
[ 501-98-4 ]
[ 929713-61-1 ]

Reference： [1]Patent: WO2012/11125,2012,A1

33
[ 501-98-4 ]
[ 1356600-14-0 ]

Reference： [1]Patent: WO2012/11125,2012,A1

34
[ 501-98-4 ]
[ 1356600-16-2 ]

Reference： [1]Patent: WO2012/11125,2012,A1

35
[ 501-98-4 ]
[ 1356598-73-6 ]

Reference： [1]Patent: WO2012/11125,2012,A1

36
[ 501-98-4 ]
[ 1356600-15-1 ]

Reference： [1]Patent: WO2012/11125,2012,A1

37
[ 501-98-4 ]
[ 824-94-2 ]
[ 1356600-13-9 ]

Yield	Reaction Conditions	Operation in experiment
91.83%	With potassium carbonate; In N,N-dimethyl-formamide; at 85℃; for 8h;Inert atmosphere;	Intermediate 32: 4-methoxybenzyl (2Z)-3-{4-[(4-methoxybenzyl) oxy] phenyl} prop-2- enoateTo a 250 mL RB flask fitted with magnetic stirrer was charged with 25 mL of DMF. To the stirred solvent were added (2Z)-3-(4-hydroxyphenyl)prop-2-enoic acid (2 g, 12.18 mmol), K2C03 (6.67 g, 48.73 mmol) and 1-(chloro methyl)-4-methoxybenzene(3.81 g, 24.36 mmol), stirred at 85 ¾ for 8-h under-nitrogen atmosphere. The RM was concentrated by removal of solvent. The crude was dissolved in ethyl acetate (100 mL). The organic layer was washed with water (50 mL) and saturated brine solution (50 mL). The organic layer was dried over anhydrous Na2S04 and the solvent was removed under reduced pressure. The product was obtained as white color solid (4.5 g, yield: 91.83%). MS (ESI, 120 eV): m/z = 403 (M-H)+ ; 1H NMR (300MHz, CDCI3): delta 7.55-7.60(d, 1 H), 7.35-7.38(d, 2H), 7.25-7.28(dd, 4H), 6.81-6.88(m, 5H), 5.09(s, 2H), 4.92(s, 2H), 3.73(s, 6H).

Reference： [1]Patent: WO2012/11125,2012,A1 .Location in patent: Page/Page column 83-84

38
peonidin 3-O-[2-O-(2-O-(trans-feruloyl)-glucosyl)-6-O-(cis-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside] [ No CAS ]
[ 2280-44-6 ]
[ 1135-24-6 ]
[ 141-82-2 ]
[ 501-98-4 ]
[ 134-01-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; at 100℃; for 1h;	General procedure: The identification of anthocyanins was carried out by standard procedures and both alkaline and acid hydrolyses (Harborne 1984). Acid hydrolysis of pigments (ca. 1 mg each) was carried out with 2N HCl (1 mL) at 100 C for 1 h. Alkaline hydrolysis of pigments (ca. 1 mg each) was carried out with 2N NaOH solution (1 mL) under degassed syringe allowed to stand for 15 min. The solution was next acidified with 2N HCl (1.1 mL) and evaporated in vacuo to dryness. The data of TLC (Rf values), HPLC (Rt-min, method 1), UV-Vis (lambdamax), and FABMS spectra are shown in Section 4.4.1.-4.4.4.

Reference： [1]Phytochemistry,2012,vol. 76,p. 73 - 77

39
[ 1392307-47-9 ]
[ 57-48-7 ]
[ 50-99-7 ]
[ 501-98-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; water; In 1,4-dioxane; at 90℃; for 3h;	General procedure: Compounds 1-8 (1-5: 1.5 mg, 6-8: 10 mg) were dissolved in 5% aqueous H2SO4-1,4-dioxane (1:1, v/v, 1-5: 2.0 mL, 6-8: 10.0 mL), and each solution was heated at 90 C for 3 h, and neutralized with Amberlite IRA-400 (OH- form). After drying in vacuo, a small aliquot of the residue was dissolved in H2O-MeOH (1:1, v/v) and analyzed by reversed-phase HPLC to identify (E)- or (Z)-p-coumaric, (E)-p-caffeic and benzoic acids, respectively, [column: COSMOSIL 5C18-MS-II, 4.6 mm I.D. - 250 mm; mobile phase A: H2O-AcOH (1000:3, v/v), B: MeCN-AcOH (1000:3, v/v), Linear gradient: mobile phase A-B (90:10?72:28, v/v, in 24.0 min); detection: UV (300 nm); flow rate: 1.0 mL/min; column temperature: ambient]. (E)-p-Coumaric acid (from 1-4, 6), (Z)-p-coumaric acid (from 5), (E)-p-caffeic acid (from 7 and 8) and benzoic acid (from 7 and 8) were identified by comparison of their retention times with those of authentic samples [(E)-p-caffeic acid: tR = 12.1 min, (E)-p-coumaric acid: tR = 17.1 min, (Z)-p-coumaric acid: tR = 18.5 min, benzoic acid: tR = 23.0 min]. In addition, the remaining parts of residue from 1-5, from which glucose and fructose were identified by TLC (ordinary phase) [CHCl3-MeOH-H2O (30:15:3, v/v/v)]], were dissolved in pyridine (0.1 mL) containing L-cysteine methyl ester hydrochloride (0.5 mg) and heated at 60 C for 1 h. o-toryl isothiocyanate (0.5 mg) in pyridine (0.1 mL) was added to the mixture and heated at 60 C for 1 h. The reaction mixture was analyzed by reversed-phase HPLC [column: COSMOSIL 5C18-AR-II, 4.6 mm I.D. - 250 mm; mobile phase: MeCN-0.05 M H3PO4 (23:77, v/v); detection: UV (250 nm); flow rate: 0.8 mL/min; column temperature: 35 C] to identify the derivatives of constituent monosaccharides in 1-5 by comparison of their retention times with those of authentic samples (tR: D-glucose; 19.7 min) (Tanaka et al., 2007). On the other hand, the remaining parts of residue from 6-8 were dissolved in water, and purified by HPLC [H2O-MeOH-AcOH (980:20:3, v/v/v), COSMOSIL 5C18-PAQ] to give D-(-)-quinic acid (6: 2.5 mg, 7: 2.0 mg, 8: 2.1 mg), which was identified by comparison of their analytical data (NMR and MS spectra and optical rotation) with that of the authentic sample.

Reference： [1]Phytochemistry,2013,vol. 92,p. 128 - 136

40
2',3',4',6'-tetra-O-acetyl-3-O-(Z)-p-coumaroylsucrose [ No CAS ]
[ 2280-44-6 ]
[ 470-23-5 ]
[ 501-98-4 ]

Reference： [1]Natural Medicines,2014,vol. 68,p. 481 - 487

41
(1R,2S)-2-hydroxycyclohexyl-2'-O-cis-p-coumaroyl-β-D-glucopyranoside [ No CAS ]
[ 2280-44-6 ]
[ 1792-81-0 ]
[ 501-98-4 ]

Reference： [1]Journal of Natural Products,2014,vol. 77,p. 1955 - 1961

42
(1S,2R)-2-hydroxycyclohexyl-2′-O-cis-p-coumaroyl-β-D-glucopyranoside [ No CAS ]
[ 2280-44-6 ]
[ 1792-81-0 ]
[ 501-98-4 ]

Reference： [1]Journal of Natural Products,2014,vol. 77,p. 1955 - 1961

43
(1S,2R)-2-hydroxycyclohexyl-6'-O-cis-p-coumaroyl-β-D-glucopyranoside [ No CAS ]
[ 2280-44-6 ]
[ 1792-81-0 ]
[ 501-98-4 ]

Reference： [1]Journal of Natural Products,2014,vol. 77,p. 1955 - 1961

44
(1R,2R)-2-hydroxycyclohexyl-2'-O-cis-p-coumaroyl-β-D-glucopyranoside [ No CAS ]
[ 501-98-4 ]
[ 69501-35-5 ]

Reference： [1]Journal of Natural Products,2014,vol. 77,p. 1955 - 1961

45
(1R,2R)-2-hydroxycyclohexyl-6'-O-cis-p-coumaroyl-β-D-glucopyranoside [ No CAS ]
[ 501-98-4 ]
[ 69501-35-5 ]

Reference： [1]Journal of Natural Products,2014,vol. 77,p. 1955 - 1961

46
(1S,2S)-2-hydroxycyclohexyl-2'-O-cis-p-coumaroyl-β-D-glucopyranoside [ No CAS ]
[ 501-98-4 ]
[ 69501-36-6 ]

Reference： [1]Journal of Natural Products,2014,vol. 77,p. 1955 - 1961

47
[ 501-98-4 ]
[ 5676-64-2 ]

Reference： [1]PLoS ONE,2015,vol. 10

48
[ 501-98-4 ]
[ 19310-29-3 ]

Reference： [1]PLoS ONE,2015,vol. 10

49
[ 501-98-4 ]
cis zosteric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfur trioxide pyridine complex; In N,N-dimethyl-formamide; acetonitrile; at 120℃; for 0.416667h;Microwave irradiation;	Zosteric acid was synthesized as already described in a previous work [16]. The cis isomer 38was obtained starting from cis 4-hydroxycinnamic acid 32 under microwave irradiation in thepresence of sulfur trioxide pyridine complex in acetonitrile (Fig 3). The final product was isolatedas sodium salt. Most of the substituted cinnamic acid derivatives were prepared in highyield (> 90%) by the Knoevenagel-Doebner procedure. In detail, compounds 2, 7, 8, 11 and 17were obtained through a one-pot reaction between the suitable substituted benzaldehyde andmalonic acid in refluxing pyridine to induce decarboxylation (Fig 4) [20]. The trans geometriesof the ethenyl pi-bonds were confirmed by proton-proton coupling constants. Cis cinnamicacid 37 was synthesized from the commercially available ethyl phenylpropiolate. The subsequenthydrogenation of alkyne in the presence of the Lindlar catalyst and pyridine in methanolled to the corresponding cis-alkene 36. Then the ester group was hydrolyzed under alkaline conditions to provide the final compound 37 (Fig 5). Esters of cinnamic acid in cis (33) or intrans configuration (23, 24) were prepared by Fischer esterification of the carboxylic group[21]. The protection of the hydroxyl group as methyl ether in the presence of iodomethane indry N,N-dimethylformamide provided the compounds 35. The hydrolysis of the ester was performedin alkaline conditions to obtain compound 34 (Fig 3).

Reference： [1]PLoS ONE,2015,vol. 10

50
[ 67-56-1 ]
[ 501-98-4 ]
[ 61240-27-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; for 1h;Reflux;	Zosteric acid was synthesized as already described in a previous work [16]. The cis isomer 38was obtained starting from cis 4-hydroxycinnamic acid 32 under microwave irradiation in thepresence of sulfur trioxide pyridine complex in acetonitrile (Fig 3). The final product was isolatedas sodium salt. Most of the substituted cinnamic acid derivatives were prepared in highyield (> 90%) by the Knoevenagel-Doebner procedure. In detail, compounds 2, 7, 8, 11 and 17were obtained through a one-pot reaction between the suitable substituted benzaldehyde andmalonic acid in refluxing pyridine to induce decarboxylation (Fig 4) [20]. The trans geometriesof the ethenyl pi-bonds were confirmed by proton-proton coupling constants. Cis cinnamicacid 37 was synthesized from the commercially available ethyl phenylpropiolate. The subsequenthydrogenation of alkyne in the presence of the Lindlar catalyst and pyridine in methanolled to the corresponding cis-alkene 36. Then the ester group was hydrolyzed under alkaline conditions to provide the final compound 37 (Fig 5). Esters of cinnamic acid in cis (33) or intrans configuration (23, 24) were prepared by Fischer esterification of the carboxylic group[21]. The protection of the hydroxyl group as methyl ether in the presence of iodomethane indry N,N-dimethylformamide provided the compounds 35. The hydrolysis of the ester was performedin alkaline conditions to obtain compound 34 (Fig 3).

Reference： [1]PLoS ONE,2015,vol. 10

51
[ 501-98-4 ]
[ 7400-08-0 ]
anti-7,8-diiodo p-hydroxy-cinnamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With iodine; In d(4)-methanol; at 40℃; for 0.0166667h;Mechanism;	TheNMR tubes contained I2 (0.3 equiv), trans- and cis- cinnamicacid derivatives in CDCl3, CD3OD-d4, prydine-d5,and acetone-d6 were remainedat 50 Cfor 1~10 min. Their 1H NMR experiments were implemented and the percentconversions of cis-isomers were 100%because the charactertic signalof cis-isomer (H-8 (8')) wasdisappeared in 1H-NMR spectrum.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 7197 - 7200

52
[ 501-98-4 ]
C₃₃H₃₇BrO₅ [ No CAS ]