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[ CAS No. 20283-92-5 ] {[proInfo.proName]}

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Chemical Structure| 20283-92-5
Chemical Structure| 20283-92-5
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Product Details of [ 20283-92-5 ]

CAS No. :20283-92-5 MDL No. :MFCD00017740
Formula : C18H16O8 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 360.31 Pubchem ID :-
Synonyms :
Labiatenic acid;Rosemary acid;NPLC 0542;RM 21A;Labiatic acid

Safety of [ 20283-92-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 20283-92-5 ]

* 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 [ 20283-92-5 ]

[ 20283-92-5 ] Synthesis Path-Downstream   1~85

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  • [ 179462-77-2 ]
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  • [ 77-78-1 ]
  • [ 54814-43-6 ]
  • 7
  • [ 20283-92-5 ]
  • [ 17176-17-9 ]
  • 3′-O-methylrosmarinic acid [ No CAS ]
  • 8
  • [ 6257-34-7 ]
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  • [ 6257-22-3 ]
  • 9
  • [ 20283-92-5 ]
  • [ 23531-69-3 ]
  • [ 59-02-9 ]
  • 10
  • rosmarinic acid 4-O-β-D-glucopyranoside [ No CAS ]
  • [ 20283-92-5 ]
  • 11
  • [ 2780-89-4 ]
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  • C25H29NO9 [ No CAS ]
  • 13
  • [ 20283-92-5 ]
  • [ 115-11-7 ]
  • (R)-3-(3,4-dihydroxy-phenyl)-acrylic acid 2-(3,4-dihydroxy-phenyl)-1-tert-butoxycarbonyl ethyl ester [ No CAS ]
  • 14
  • [ 20283-92-5 ]
  • C18H18O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With 5%-palladium/activated carbon; hydrogen; In acetone; at 20℃; for 3h; <strong>[20283-92-5]Rosmarinic acid</strong> (3) (300 mg) was resolved in acetone (5 mL), after which 5% palladium on activated carbon (40 mg) was added to the solution. The reaction mixture was stirred under a hydrogen atmosphere at room temperature for 3 h and filtered through celite, affording 12 as colorless oil (296 mg,98% yield). Using compound 8 as a starting material, compound 13 was obtained as a colorless oil (95% yield) by the same procedure.
  • 16
  • [ 64-17-5 ]
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  • ethyl ester of rosmarinic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
800 mg With sulfuric acid; <strong>[20283-92-5]Rosmarinic acid</strong> (1g) was dissolved in absolute ethanol (25ml), and concentrated sulfuric acid (1ml)was added.The mixture was kept stirring overnight, and water (20ml) was then added.The mixture was extracted with ethyl acetate; the organic layer was washed with water and dried over anhydrous sodium sulfate, and the solvent was evaporated. The crude product was purified using silica column chromatography by eluting with ethyl acetate-methanol (100:1) to yield ethyl rosmarinate (800mg). The spectroscopic (NMR and mass spectra) data were in agreement with the structure. The structure of ethyl rosmarinate is shown in Fig. 1.
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  • [ 179128-84-8 ]
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  • [ 179129-02-3 ]
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  • [ 139-85-5 ]
  • neutral aqueous oxalacetic acid [ No CAS ]
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  • 31
  • [ 20283-92-5 ]
  • (E)-3-(3,4-Diacetoxy-phenyl)-acrylic acid (R)-2-(3,4-diacetoxy-phenyl)-1-methoxycarbonyl-ethyl ester [ No CAS ]
  • 33
  • [ 863107-05-5 ]
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  • 34
  • [ 20283-92-5 ]
  • (R)-2-(3,4-dihydroxyphenyl)-1-carbamoylethyl 3-(3,4-dihydroxyphenyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With oxalyl dichloride; ammonia; In tetrahydrofuran; at 20℃;Inert atmosphere; <strong>[20283-92-5]Rosmarinic acid</strong> (1, 99.2 mg, 0.275 mmol) was dissolved in of THF (4 mL) with ammonia gas, and stirred at room temperature for 14 h. The reaction mixture was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (MeOH-CHCl3) (1:1 v/v) and reverse phase column chromatography on C18 -coated silica gel (MeOH-H2O) (1:3 v/v) to give a title compound (94.8 mg, 96%) as a yellow solid. Mp: 198-201 C, IR : 3193, 1682, 1576, 1517, 1441, 1254, 1156, 1114, 975, 809 cm-1. 1H NMR (500 MHz, DMSO-d6) delta: 7.35 (d, 1H, J = 15.8 Hz), 7.02 (d, 1H, J = 2.1 Hz), 6.89 (dd, 1H, J = 2.0, 8.0 Hz), 6.72 (d, 1H, J = 8.0 Hz), 6.65 (d, 1H, J = 2.0 Hz), 6.58 (d, 1H, J = 8.0 Hz), 6.47 (dd, 1H, J = 2.0, 8.0 Hz), 6.16 (d, 1H, J = 15.8 Hz), 4.83 (dd, 1H, J = 3.2, 10.0 Hz), 2.99 (dd, J = 2.8, 14.3 Hz), 2.73 (dd, 1H, J = 10.0, 14.3 Hz). 13C NMR (125 MHz, DMSO-d6) delta: 172.7, 166.5, 148.8, 146.2, 145.1, 144.4, 143.7, 130.3, 125.6, 120.8, 199.8, 116.8, 116.0, 115.5, 115.2, 115.0, 76.4, 37.5. High-resolution MS calcd for C18H18O2 (M+H): 360.1083. Found: 360.1067. All spectral data agreed with previously reported data [1].
  • 35
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  • [ 75-31-0 ]
  • (R)-3-(3,4-dihydroxy-phenyl)-acrylic acid 2-(3,4-dihydroxy-phenyl)-1-isopropylcarbamoyl ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl; at 20℃; for 0.5h;Reactivity (does not react); In order to confirm the antioxidant activity of the compounds, a DPPH method was employed. DPPH (l,l-diphenyl-2-picrylhydrazyl) is a chromogenic radical and thus, can be used to directly confirm the radical scavenging activity of the samples. The samples were dissolved in 4 ml of distilled water or solvent (methanol) and then, mixed well with 1 ml of 100 muM DPPH. Subsequently, the samples were incubated at room temperature for 30 minutes. The absorbance of the remaining DPPH was measured at 517 nm. As a blank of the present experiment, distilled water or solvent was used, and as a control, an experimental group composed only of DPPH in distilled water or solvent without the sample was used. Further, vitamin C was used as a positive control. As a result, the antioxidant activity was expressed as percentages of the absorbance of each hydrolysate relative to the absorbance of control, as calculated by the following equation 1.[81][82] (Experimental Equation 1)[83]RSAW = Ab5 f hydfKylate chi l00 Abs of Control[84] (RSA: Radical Scavenging Activity)[85]
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  • [ 1020400-23-0 ]
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  • [ 57-50-1 ]
  • rosmarinic acid O-α-D-glucoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
dextransucrase; In water; dimethyl sulfoxide; at 30℃; for 22h;pH 5.2;Sodium acetate buffer; Calcium chloride; Enzymatic reaction;Product distribution / selectivity; Example 6Enzymatic Synthesis of O-alpha-D-Glycosides of Caffeic Acid, 3,4-Dihydroxyhydrocinnamic Acid (Hydrocaffeic Acid) and Rosmarinic AcidReaction media were prepared as described in example 1, Taxifolin being replaced by Caffeic acid (SIGMA, reference C 0625), or by 3,4-Dihydroxyhydrocinnamic acid (ALDRICH, reference D10,980-0) or by <strong>[20283-92-5]Rosmarinic acid</strong> (FLUKA, reference 44699; the concentration of <strong>[20283-92-5]Rosmarinic acid</strong> in the reaction medium was 1 g/L).After 21 hours of incubation, a sample of each reaction medium was diluted 5 times with a solution containing methanol and water in the proportions of 40/60 and then analysed by HPLC (method 1).The results are reported in the following table. Retention time, Identification (theroretical Glucosyl acceptor minutes m/z [M - H] molecular weight) Caffeic acid 19.53 178.97 Caffeic acid (180) (chromatogram at 322 nm in 15.46 341.09 Caffeic acid monoglucoside (342) FIG. 20) 14.62 503.16 Caffeic acid diglucoside (504) 3,4- 18.72 343.02 Hydrocaffeic acid monoglucoside Dihydroxyhydrocinnamic (344) acid (hydrocaffeic acid) 17.93 505.05 Hydrocaffeic acid diglucoside (506) (chromatogram at 278 nm in 17.80 180.96 Hydrocaffeic acid (182) FIG. 21) 17.50 343.02 Hydrocaffeic acid monoglucoside (344) 17.06 667.21 Hydrocaffeic acid triglucoside (668) 16.23 829.25 Hydrocaffeic acid tetraglucoside (830) 16.01 505.05 Hydrocaffeic acid diglucoside (506) 15.70 992.36 Hydrocaffeic acid pentaglucoside (992) 14.70 667.21 Hydrocaffeic acid triglucoside (668) 13.92 829.39 Hydrocaffeic acid tetraglucoside (830) 13.22 991.50 Hydrocaffeic acid pentaglucoside (992) 12.61 1153.60 Hydrocaffeic acid hexaglucoside (1154) 12.08, 11.21 No. Polymerization degree higher than 6 <strong>[20283-92-5]Rosmarinic acid</strong> 28.36 359.09 <strong>[20283-92-5]Rosmarinic acid</strong> (360) (chromatogram at 295 nm in 27.18 521.16 <strong>[20283-92-5]Rosmarinic acid</strong> monoglucoside FIG. 22) (522) It is thus possible according to the described method to synthesize the new glucosylated derivatives of Caffeic acid, Hydrocaffeic acid and <strong>[20283-92-5]Rosmarinic acid</strong>: the resulting products are a family of substances containing at least monoglycosylated, diglucosylated, triglucosylated and tetraglucosylated derivatives. As far as Hydrocaffeic acid is concerned, it clearly appears that both hydroxyl groups have been substituted: indeed, it can be seen at least two series of derivatives, both containing at least monoglucosylated (344), diglucosylated (506), triglucosylated (668), tetraglucosylated (830) and pentaglucosylated (992) derivatives. This shows that in some cases that can not be predicted by a skilled man, both hydroxylated groups can accept a glucose moiety.
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  • [ 402-49-3 ]
  • [ 18107-18-1 ]
  • [ 1115211-08-9 ]
YieldReaction ConditionsOperation in experiment
84% TMS-diazomethane (2.0 M in Et2O, 7.9 mL, 15.8 mmol, 0.95 equiv) was added in small portions over 1 h to a solution of rosmarinic acid (5, 6.00 g, 16.7 mmol, 1.0 equiv) in THF:MeOH (10:1, 110 mL) at -78 0C. Upon completion, the reaction contents were allowed to warm to 25 0C over 1 h, concentrated directly, and filtered through a short plug of silica gel (CH2Cl2:Me0H, 19:1) . The resultant thick brown oil was dried thoroughly under high vacuum to provide the desired ester intermediate that was carried forward without any additional purification. Next, p-trifluoromethylbenzyl bromide (7.40 mL, 48.0 mmol, 6.0 equiv), K2CO3 (6.60 g, 48.0 mmol, 6.0 equiv), and KI (catalytic) were added sequentially and in single portions to a solution of half of the crude ester just prepared (8.0 mmol, 1.0 equiv) in DMF (30 mL) at 25 0C. The resultant reaction mixture was then stirred at 60 0C for 8 h, and at 25 0C for 16 h. Upon completion, the reaction contents were carefully quenched by the addition of 1 M aqueous HCl (until gas evolution ceased), poured into water (50 mL) , and extracted with EtOAc (2 x 100 itiL) . The combined organic layers were then washed with 1 M aqueous HCl (50 mL) , saturated aqueous NaHCO3 (50 mL) and brine (50 mL) , dried (MgSO4), and concentrated. The resultant crude material was purified by flash column chromatography (silica gel, hexanes: EtOAc: CH2Cl2, 17 : 1 :2?5 :4 : 1) to afford dienophile 27 (6.00 g, 84% yield over 2 steps) as a white amorphous solid. 27: Rf = 0.45 (silica gel, hexanes : EtOAc : CH2Cl2, 3:1:1); IR (film) {max 1751, 1715, 1625, 1598, 1511, 1324, 1265, 1160, 1120, 1065, 1016, 824, 736 cm-1; 1H NMR (400 MHz, CDCl3) delta 7.66-7.49 (m, 17 H), 7.11-7.08 (m, 2 H), 6.92- 6.81 (m, 4 H), 6.29 (d, J = 16.0 Hz, 1 H), 5.36 (dd, J = 8.0, 4.8 Hz, 1 H), 5.23 (s, 2 H), 5.19 (s, 2 H), 5.17 (s, 2 H), 5.16 (s, 2 H), 3.71 (s, 3 H), 3.18 (dd, J" = 14.4, 5.0 Hz, 1 H), 3.11 (dd, J = 14.4, 8.4 Hz, 1 H); 13C NMR (75 MHz, CDCl3) delta 170.1, 166.0, 150.8, 148.6, 148.5, 147.7, 145.5, 141.2, 141.1, 140.7, 140.5, 127.9, 127.2, 127.2, 127.1, 125.8, 125.4, 125.3, 125.3, 123.3, 122.7, 122.2, 116.2, 115.2, 114.9, 114.0, 113.5, 72.8, 70.5, 70.3, 69.9, 52.2, 36.9; HRMS (FAB) calcd for C5IH38Fi2O8+ [M+] 1006.2375, found 1006.2424.
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  • [ 1174681-32-3 ]
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  • [ 20283-92-5 ]
  • C18H17NO5 [ No CAS ]
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  • C18H17NO5 [ No CAS ]
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  • [ 20283-92-5 ]
  • C18H18O9 [ No CAS ]
  • C18H18O9 [ No CAS ]
  • 52
  • [ 20283-92-5 ]
  • C18H18O9 [ No CAS ]
  • C18H18O9 [ No CAS ]
  • [ 331-39-5 ]
  • [ 23028-17-3 ]
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  • C17H18O7 [ No CAS ]
  • C17H18O7 [ No CAS ]
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  • [ 420-04-2 ]
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  • [ 1310802-43-7 ]
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  • [ 54814-41-4 ]
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  • [ 74-88-4 ]
  • [ 54814-43-6 ]
YieldReaction ConditionsOperation in experiment
74% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 96h; A stirred solution of 3 (180 mg, 0.5 mmol) in DMF (5 mL) was added to anhydrous K2CO3 (520 mg,3.75 mmol) followed by methyl iodide (0.24 mL, 3.75 mmol). The reaction mixture was heated to 60 C for 2 d, after which methyl iodide (0.24 mL, 3.75 mmol) was added and heating was continued for a further 2 d. The mixture was cooled to room temperature and quenched by the addition of H2O (30 mL), after which the resulting mixture was extracted with Et2O (3*40 mL) and the combined organic phases were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc:petroleum ether = 2:5) to afford 8 as a colorless oil (160 mg, 74% yield).
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  • [ 70-18-8 ]
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  • C28H31N3O14S [ No CAS ]
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  • [ 999-81-5 ]
  • [ 76-05-1 ]
  • [ 1314894-98-8 ]
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  • [ 1356166-50-1 ]
  • [ 1356166-49-8 ]
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  • [ 112-55-0 ]
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  • [ 203798-74-7 ]
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  • [ 1246887-09-1 ]
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  • [ 1510460-41-9 ]
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  • [ 20283-92-5 ]
  • C42H48O8Si [ No CAS ]
  • 82
  • [ 20283-92-5 ]
  • [ 111-27-3 ]
  • rosmarinic acid hexyl ester [ No CAS ]
  • 83
  • [ 52-90-4 ]
  • [ 20283-92-5 ]
  • 5''′-S-cysteinylrosmarinic acid [ No CAS ]
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  • [ 7585-39-9 ]
  • [ 1301620-15-4 ]
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  • C23H28O8 [ No CAS ]
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