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Cas Database

2052-63-3

2052-63-3

Identification

  • Product Name:Retinol, 13-cis-

  • CAS Number: 2052-63-3

  • EINECS:

  • Molecular Weight:286.458

  • Molecular Formula: C20H30O

  • HS Code:

  • Mol File:2052-63-3.mol

Synonyms:(13Z)-Retinol;13-cis-Retinol;13-cis-Vitamin A;Neovitamin A;Neovitamin A1;neo-Retinol;

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Safety information and MSDS view more

  • Pictogram(s):Xi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritation

  • 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

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  • Manufacture/Brand:TRC
  • Product Description:13-cis-Retinol
  • Packaging:1mg
  • Price:$ 235
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  • Manufacture/Brand:TRC
  • Product Description:13-cis-Retinol
  • Packaging:10mg
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:13-cis-Retinol
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Relevant articles and documentsAll total 22 Articles be found

Hubbard

, p. 4662,4664 (1956)

Z -isomerization of retinoids through combination of monochromatic photoisomerization and metal catalysis

Kahremany, Shirin,Sander, Christopher Lane,Tochtrop, Gregory P.,Kubas, Adam,Palczewski, Krzysztof

supporting information, p. 8125 - 8139 (2019/09/19)

Catalytic Z-isomerization of retinoids to their thermodynamically less stable Z-isomer remains a challenge. In this report, we present a photochemical approach for the catalytic Z-isomerization of retinoids using monochromatic wavelength UV irradiation treatment. We have developed a straightforward approach for the synthesis of Z-retinoids in high yield, overcoming common obstacles normally associated with their synthesis. Calculations based on density functional theory (DFT) have allowed us to correlate the experimentally observed Z-isomer distribution of retinoids with the energies of chemically important intermediates, which include ground- and excited-state potential energy surfaces. We also demonstrate the application of the current method by synthesizing gram-scale quantities of 9-cis-retinyl acetate 9Z-a. Operational simplicity and gram-scale ability make this chemistry a very practical solution to the problem of Z-isomer retinoid synthesis.

Catalytic synthesis of 9-cis-retinoids: Mechanistic insights

Kahremany, Shirin,Kubas, Adam,Tochtrop, Gregory P.,Palczewski, Krzysztof

supporting information, p. 10581 - 10595 (2019/07/22)

The regioselective Z-isomerization of thermodynamically stable all-trans retinoids remains challenging, and ultimately limits the availability of much needed therapeutics for the treatment of human diseases. We present here a novel, straightforward approach for the catalytic Z-isomerization of retinoids using conventional heat treatment or microwave irradiation. A screen of 20 transition metal-based catalysts identified an optimal approach for the regioselective production of Z-retinoids. The most effective catalytic system was comprised of a palladium complex with labile ligands. Several mechanistic studies, including isotopic H/D exchange and state-of-the-art quantum chemical calculations using coupled cluster methods indicate that the isomerization is initiated by catalyst dimerization followed by the formation of a cyclic, six-membered chloropalladate catalyst-substrate adduct, which eventually opens to produce the desired Z-isomer. The synthetic development described here, combined with thorough mechanistic analysis of the underlying chemistry, highlights the use of readily available transition metal-based catalysts in straightforward formats for gram-scale drug synthesis.

METHOD FOR SYNTHESIS OF 9-CIS-BETA-CAROTENE AND FORMULATIONS THEREOF

-

, (2017/12/29)

The present invention relates to a method for total chemical synthesis of 9-cis-β-carotene (9CBC), and further provides stable formulations thereof.

Substrate specificity and subcellular localization of the aldehyde-Alcohol redox-Coupling reaction in carp cones

Sato, Shinya,Fukagawa, Takashi,Tachibanaki, Shuji,Yamano, Yumiko,Wada, Akimori,Kawamura, Satoru

, p. 36589 - 36597 (2014/01/17)

Our previous study suggested the presence of a novel conespecific redox reaction that generates 11-cis-retinal from 11-cisretinol in the carp retina. This reaction is unique in that 1) both 11-cis-retinol and all-trans-retinal were required to produce 11-cis-retinal; 2) together with 11-cis-retinal, all-trans-retinol was produced at a 1:1 ratio; and 3) the addition of enzyme cofactors such as NADP(H) was not necessary. This reaction is probably part of the reactions in a cone-specific retinoid cycle required for cone visual pigment regeneration with the use of 11-cis-retinol supplied from Mueller cells. In this study, using purified carp cone membrane preparations, we first confirmed that the reaction is a redox-coupling reaction between retinals and retinols. We further examined the substrate specificity, reaction mechanism, and subcellular localization of this reaction. Oxidation was specific for 11-cis-retinol and 9-cis-retinol. In contrast, reduction showed low specificity: many aldehydes, including all-trans-, 9-cis-, 11-cis-, and 13-cis-retinals and even benzaldehyde, supported the reaction. On the basis of kinetic studies of this reaction (aldehyde-alcohol redox-coupling reaction), we found that formation of a ternary complex of a retinol, an aldehyde, and a postulated enzyme seemed to be necessary, which suggested the presence of both the retinol- and aldehydebinding sites in this enzyme. A subcellular fractionation study showed that the activity is present almost exclusively in the cone inner segment. These results suggest the presence of an effective production mechanism of 11-cis-retinal in the cone inner segment to regenerate visual pigment.

An improved synthesis of retinal (Vitamin A Aldehyde)

Sacolick, Davidson A.,Curley, Robert W.

, p. 325 - 327 (2013/07/26)

-

Process route upstream and downstream products

Process route

Conditions
Conditions Yield
With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 ℃; for 1h;
Conditions
Conditions Yield
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 1.5h;
93%
1-acetoxy-3,7-dimethyl-8-(tetrahydropyran-2-yl)oxy-9-phenylsulfonyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2(E),6(E)-nonadiene
103905-07-3

1-acetoxy-3,7-dimethyl-8-(tetrahydropyran-2-yl)oxy-9-phenylsulfonyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2(E),6(E)-nonadiene

2-cis-Vitamin-A
2052-63-3

2-cis-Vitamin-A

11-cis-retinol
22737-96-8

11-cis-retinol

RETINOL
68-26-8

RETINOL

Conditions
Conditions Yield
With potassium methanolate; In cyclohexane; at 38 ℃; for 2h;
77%
With potassium methanolate; In cyclohexane; at 38 ℃; for 2h; Title compound not separated from byproducts;
1-acetoxy-3,7-dimethyl-8-(tetrahydropyran-2-yl)oxy-9-phenylsulfonyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2(E),6(E)-nonadiene
103905-07-3

1-acetoxy-3,7-dimethyl-8-(tetrahydropyran-2-yl)oxy-9-phenylsulfonyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2(E),6(E)-nonadiene

2-cis-Vitamin-A
2052-63-3

2-cis-Vitamin-A

11-cis-retinol
22737-96-8

11-cis-retinol

RETINOL
68-26-8

RETINOL

Conditions
Conditions Yield
With potassium methanolate; In cyclohexane; at 38 ℃; for 2h;
77%
With potassium methanolate; In cyclohexane; at 38 ℃; for 2h; Title compound not separated from byproducts;
Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: BuLi / tetrahydrofuran
2: P2O5
3: MeOK / cyclohexane; hexane; tetrahydrofuran / 1.) r.t., 1 h, 2.) 40 deg C, 1 h
With n-butyllithium; potassium methanolate; phosphorus pentoxide; In tetrahydrofuran; hexane; cyclohexane;
Multi-step reaction with 2 steps
1: 1.) BuLi, NaI / 1.) THF, hexane, -78 deg C, 1 h, 2.) -78 deg C, 4 h; r.t., 1 h
2: MeOK / cyclohexane; hexane; tetrahydrofuran / 1.) r.t., 1 h, 2.) 40 deg C, 1 h
With n-butyllithium; potassium methanolate; sodium iodide; In tetrahydrofuran; hexane; cyclohexane;
Multi-step reaction with 2 steps
1: 1.) BuLi, NaI / 1.) THF, hexane, -78 deg C, 1 h, 2.) -78 deg C, 4 h; r.t., 1 h
2: MeOK / cyclohexane; hexane; tetrahydrofuran / 1.) r.t., 1 h, 2.) 40 deg C, 1 h
With n-butyllithium; potassium methanolate; sodium iodide; In tetrahydrofuran; hexane; cyclohexane;
Multi-step reaction with 3 steps
1: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h
2: 99 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature
3: MeOK / cyclohexane / 2 h / 38 °C
With n-butyllithium; potassium methanolate; toluene-4-sulfonic acid; In dichloromethane; cyclohexane;
Multi-step reaction with 3 steps
1: 93 percent / n-BuLi / tetrahydrofuran / 5 h / -78 °C
2: p-toluenesulfonic acid / CH2Cl2
3: MeOK / cyclohexane / 2 h / 38 °C
With n-butyllithium; potassium methanolate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; cyclohexane;
Conditions
Conditions Yield
Multi-step reaction with 3 steps
1: BuLi / tetrahydrofuran
2: P2O5
3: MeOK / cyclohexane; hexane; tetrahydrofuran / 1.) r.t., 1 h, 2.) 40 deg C, 1 h
With n-butyllithium; potassium methanolate; phosphorus pentoxide; In tetrahydrofuran; hexane; cyclohexane;
Multi-step reaction with 2 steps
1: 1.) BuLi, NaI / 1.) THF, hexane, -78 deg C, 1 h, 2.) -78 deg C, 4 h; r.t., 1 h
2: MeOK / cyclohexane; hexane; tetrahydrofuran / 1.) r.t., 1 h, 2.) 40 deg C, 1 h
With n-butyllithium; potassium methanolate; sodium iodide; In tetrahydrofuran; hexane; cyclohexane;
Multi-step reaction with 2 steps
1: 1.) BuLi, NaI / 1.) THF, hexane, -78 deg C, 1 h, 2.) -78 deg C, 4 h; r.t., 1 h
2: MeOK / cyclohexane; hexane; tetrahydrofuran / 1.) r.t., 1 h, 2.) 40 deg C, 1 h
With n-butyllithium; potassium methanolate; sodium iodide; In tetrahydrofuran; hexane; cyclohexane;
Multi-step reaction with 3 steps
1: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h
2: 99 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature
3: MeOK / cyclohexane / 2 h / 38 °C
With n-butyllithium; potassium methanolate; toluene-4-sulfonic acid; In dichloromethane; cyclohexane;
Multi-step reaction with 3 steps
1: 93 percent / n-BuLi / tetrahydrofuran / 5 h / -78 °C
2: p-toluenesulfonic acid / CH2Cl2
3: MeOK / cyclohexane / 2 h / 38 °C
With n-butyllithium; potassium methanolate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; cyclohexane;
Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: P2O5
2: MeOK / cyclohexane; hexane; tetrahydrofuran / 1.) r.t., 1 h, 2.) 40 deg C, 1 h
With potassium methanolate; phosphorus pentoxide; In tetrahydrofuran; hexane; cyclohexane;
Multi-step reaction with 2 steps
1: 99 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature
2: MeOK / cyclohexane / 2 h / 38 °C
With potassium methanolate; toluene-4-sulfonic acid; In dichloromethane; cyclohexane;
Multi-step reaction with 2 steps
1: p-toluenesulfonic acid / CH2Cl2
2: MeOK / cyclohexane / 2 h / 38 °C
With potassium methanolate; toluene-4-sulfonic acid; In dichloromethane; cyclohexane;
Conditions
Conditions Yield
Multi-step reaction with 5 steps
1: SeO2, salicylic acid, tert-butyl hydroperoxide / CH2Cl2 / 27 h / Ambient temperature
2: PDC / CH2Cl2 / 10 h / Ambient temperature
3: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h
4: 99 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature
5: MeOK / cyclohexane / 2 h / 38 °C
With tert.-butylhydroperoxide; dipyridinium dichromate; n-butyllithium; selenium(IV) oxide; potassium methanolate; toluene-4-sulfonic acid; salicylic acid; In dichloromethane; cyclohexane;
Multi-step reaction with 4 steps
1: SeO2, salicylic acid, tert-butyl hydroperoxide / CH2Cl2 / 27 h / Ambient temperature
2: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h
3: 99 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature
4: MeOK / cyclohexane / 2 h / 38 °C
With tert.-butylhydroperoxide; n-butyllithium; selenium(IV) oxide; potassium methanolate; toluene-4-sulfonic acid; salicylic acid; In dichloromethane; cyclohexane;
Conditions
Conditions Yield
(9Ξ)-O-acetyl-retinol; With sodium hydroxide; In ethanol; water; at 40 ℃; for 0.5h; Inert atmosphere; Darkness;
With pyridine; In Methyl formate; at 0 ℃; for 2h; Reagent/catalyst; Catalytic behavior;
90%

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