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Cas Database

65646-68-6

65646-68-6

Identification

Synonyms:(4-Hydroxyphenyl)retinamide;4-HPR;Fenretinide;N-(4-Hydroxyphenyl)-all-trans-retinamide;N-(4-Hydroxyphenyl)retinamide;RII retinamide;Retinoic acidp-hydroxyphenylamide;Ro 22-4667;all-trans-4'-Hydroxyretinanilide;all-trans-N-(4-Hydroxyphenyl)retinamide;

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Safety information and MSDS view more

  • Pictogram(s):

  • Hazard Codes:T

  • Signal Word:Danger

  • Hazard Statement:H302 Harmful if swallowedH312 Harmful in contact with skin H315 Causes skin irritation H319 Causes serious eye irritation H332 Harmful if inhaled H335 May cause respiratory irritation H360 May damage fertility or the unborn child

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price view more

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase
  • Manufacture/Brand:Usbiological
  • Product Description:HPR
  • Packaging:100ul
  • Price:$ 499
  • Delivery:In stock
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  • Manufacture/Brand:Usbiological
  • Product Description:HPR
  • Packaging:96Tests
  • Price:$ 729
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:Fenretinide
  • Packaging:50mg
  • Price:$ 260
  • Delivery:In stock
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  • Manufacture/Brand:Tocris
  • Product Description:Fenretinide ≥98%(HPLC)
  • Packaging:10
  • Price:$ 161
  • Delivery:In stock
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  • Manufacture/Brand:Tocris
  • Product Description:Fenretinide ≥98%(HPLC)
  • Packaging:50
  • Price:$ 674
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:all-trans-N-(4-Hydroxyphenyl)retinamide >98.0%(HPLC)
  • Packaging:100mg
  • Price:$ 572
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:all-trans-N-(4-Hydroxyphenyl)retinamide >98.0%(HPLC)
  • Packaging:10mg
  • Price:$ 143
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Retinoic acid p-hydroxyanilide ≥98% (HPLC), powder
  • Packaging:5mg
  • Price:$ 178
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:4-Hydroxyphenylretinamide A synthetic amide of all-
  • Packaging:5mg
  • Price:$ 161.87
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:ANTI-HPR (CENTER) antibody produced in rabbit IgG fraction of antiserum, buffered aqueous solution
  • Packaging:400ul
  • Price:$ 361
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Relevant articles and documentsAll total 6 Articles be found

Fenretinide derivatives act as disrupters of interactions of serum retinol binding protein (sRBP) with transthyretin and the sRBP receptor

Campos-Sandoval, José Angel,Redondo, Clara,Kinsella, Gemma K.,Pal, Akos,Jones, Geraint,Eyre, Gwen S.,Hirst, Simon C.,Findlay, John B. C.

experimental part, p. 4378 - 4387 (2011/09/14)

Serum retinol binding protein (sRBP) is released from the liver as a complex with transthyretin (TTR), a process under the control of dietary retinol. Elevated levels of sRBP may be involved in inhibiting cellular responses to insulin and in generating first insulin resistance and then type 2 diabetes, offering a new target for therapeutic attack for these conditions. A series of retinoid analogues were synthesized and examined for their binding to sRBP and their ability to disrupt the sRBP-TTR and sRBP-sRBP receptor interactions. A number inhibit the sRBP-TTR and sRBP-sRBP receptor interactions as well as or better than Fenretinide (FEN), presenting a potential novel dual mechanism of action and perhaps offering a new therapeutic intervention against type 2 diabetes and its development. Shortening the chain length of the FEN derivative substantially abolished binding to sRBP, indicating that the strength of the interaction lies in the polyene chain region. Differences in potency against the sRBP-TTR and sRBP-sRBP receptor interactions suggest variant effects of the compounds on the two loops of sRBP guarding the entrance of the binding pocket that are responsible for these two protein-protein interactions.

Solid phase-assisted synthesis and screening of a small library of N-(4-hydroxyphenyl)retinamide (4-HPR) analogs

Mershon, Serena M.,Anding, Allyson L.,Chapman, Jason S.,Clagett-Dame, Margaret,Stonerock, Laura A.,Curley Jr., Robert W.

, p. 836 - 840 (2007/10/03)

Using solid phase-assisted synthesis and purification, a 49 member library of analogs of the mammary tumor chemopreventive retinoid N-(4-hydroxyphenyl)retinamide (4-HPR) has been prepared. After prescreening for growth inhibitory activity in human mammary tumor cells (MCF-7) in culture, most of those analogs which showed activity (12 of them) were assayed for apoptosis-inducing activity in the MCF-7 cells. At least 3 of the analogs (13, 24, and 28) showed activity approaching that of 4-HPR.

A simple, general and efficient method for O and N-retinoylation. Application to the synthesis of 2-retinoyl-lecithin

Sangmam, Charles,Winum, Jean-Yves,Lucas, Marc,Montero, Jean-Louis,Chavis, Claude

, p. 2945 - 2958 (2007/10/03)

The synthesis of the new 1-stearoyl-2-retinoyl-glycero-3- phosphorylcholine by coupling of retinoic acid and lysolecithin with DCC- DMAP (1.2 eq.) is reported. This method is applied to O and N-retinoylation of uncharged organic substrates such as aliphatic alcohols, free hydroxyl anomeric sugars, aromatic amines and C-protected α-aminoacids.

Process route upstream and downstream products

Process route

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

4-amino-phenol
123-30-8

4-amino-phenol

N-(4-hydroxyphenyl)-all-trans-retinamide
65646-68-6

N-(4-hydroxyphenyl)-all-trans-retinamide

Conditions
Conditions Yield
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; for 1h; Ambient temperature;
80%
all-trans-retinoic-acid; With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 0.5h;
4-amino-phenol; With dmap; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 4h;
48%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;
retinoic acid, t-butyl mixed anhydride

retinoic acid, t-butyl mixed anhydride

4-amino-phenol
123-30-8

4-amino-phenol

N-(4-hydroxyphenyl)-all-trans-retinamide
65646-68-6

N-(4-hydroxyphenyl)-all-trans-retinamide

Conditions
Conditions Yield
With pyridine; In ethyl acetate; at 3 - 5 ℃; for 2.5h; Product distribution / selectivity;
retinoic acid, isobutyl mixed carbonate

retinoic acid, isobutyl mixed carbonate

4-amino-phenol
123-30-8

4-amino-phenol

N-(4-hydroxyphenyl)-all-trans-retinamide
65646-68-6

N-(4-hydroxyphenyl)-all-trans-retinamide

Conditions
Conditions Yield
retinoic acid, isobutyl mixed carbonate; 4-amino-phenol; In tert-butyl methyl ether; N,N-dimethyl-formamide; at 10 ℃; for 2.16667h;
With hydrogenchloride; In tert-butyl methyl ether; water; N,N-dimethyl-formamide; at 10 ℃; Product distribution / selectivity;
retinoyl chloride
53839-60-4

retinoyl chloride

4-amino-phenol
123-30-8

4-amino-phenol

N-(4-hydroxyphenyl)-all-trans-retinamide
65646-68-6

N-(4-hydroxyphenyl)-all-trans-retinamide

Conditions
Conditions Yield
In benzene; at 10 - 15 ℃;
With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;
With pyridine; at 0 - 20 ℃;
all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

N-(4-hydroxyphenyl)-all-trans-retinamide
65646-68-6

N-(4-hydroxyphenyl)-all-trans-retinamide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: hexachloroacetone; triphenylphosphine-resin / tetrahydrofuran / 1 h / 0 °C
2: pyridine / 0 - 20 °C
With pyridine; 1,1,1,3,3,3-hexachloro-propan-2-one; triphenylphosphine-resin; In tetrahydrofuran;
Multi-step reaction with 2 steps
1: SOCl2; DMF / 0.75 h / 0 °C
2: triethylamine / dimethylformamide / 2 h / 20 °C
With thionyl chloride; triethylamine; N,N-dimethyl-formamide; In N,N-dimethyl-formamide;
Multi-step reaction with 2 steps
1: phosphorus trichloride / benzene / 4 h / 25 - 30 °C
2: benzene / 10 - 15 °C
With phosphorus trichloride; In benzene;
C<sub>26</sub>H<sub>38</sub>O<sub>3</sub>

C26H38O3

4-amino-phenol
123-30-8

4-amino-phenol

N-(4-hydroxyphenyl)-all-trans-retinamide
65646-68-6

N-(4-hydroxyphenyl)-all-trans-retinamide

Conditions
Conditions Yield
In acetonitrile; at 0 - 10 ℃; Product distribution / selectivity;
(2,5,7,8-tetramethyl-2R-[4R,8R,12-trimethyltridecyl]chroman-6-yloxy)acetic acid
261929-52-6

(2,5,7,8-tetramethyl-2R-[4R,8R,12-trimethyltridecyl]chroman-6-yloxy)acetic acid

N-(4-hydroxyphenyl)-all-trans-retinamide
65646-68-6

N-(4-hydroxyphenyl)-all-trans-retinamide

fenretinide

fenretinide

Conditions
Conditions Yield
With 4-methyl-N-methylpyridinium p-toluenesulfonate salt; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 2.25h; Inert atmosphere; Cooling with ice;
95%
C<sub>91</sub>H<sub>182</sub>O<sub>47</sub>

C91H182O47

N-(4-hydroxyphenyl)-all-trans-retinamide
65646-68-6

N-(4-hydroxyphenyl)-all-trans-retinamide

C<sub>117</sub>H<sub>213</sub>NO<sub>48</sub>

C117H213NO48

Conditions
Conditions Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 24h;
N-(4-hydroxyphenyl)-all-trans-retinamide
65646-68-6

N-(4-hydroxyphenyl)-all-trans-retinamide

butyryl chloride
141-75-3

butyryl chloride

4-{(2E,4E,6E,8E)-[3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoylamino]}-phenyl butanoate

4-{(2E,4E,6E,8E)-[3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoylamino]}-phenyl butanoate

Conditions
Conditions Yield
With 4-methyl-morpholine; In dichloromethane; at 0 ℃; for 0.5h;
91%
propionic acid
802294-64-0,79-09-4

propionic acid

N-(4-hydroxyphenyl)-all-trans-retinamide
65646-68-6

N-(4-hydroxyphenyl)-all-trans-retinamide

4-{(2E,4E,6E,8E)-[3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoylamino]}-phenyl propionate
75858-21-8

4-{(2E,4E,6E,8E)-[3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoylamino]}-phenyl propionate

Conditions
Conditions Yield
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide; for 5h;
76%

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