CN101851171A - Preparation method of D-panthenol - Google Patents
Preparation method of D-panthenol Download PDFInfo
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- CN101851171A CN101851171A CN 201010163575 CN201010163575A CN101851171A CN 101851171 A CN101851171 A CN 101851171A CN 201010163575 CN201010163575 CN 201010163575 CN 201010163575 A CN201010163575 A CN 201010163575A CN 101851171 A CN101851171 A CN 101851171A
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Abstract
The invention relates to a preparation method of D-panthenol. D-(-)-pantolactone is reacted with 3-amino-1-propanol in the absence of solvent to obtain the high-purity D-panthenol, and the overall yield is more than 80%.
Description
Technical field
The present invention relates to a kind of preparation method of D-panthenol, particularly the preparation method of high-optical-purity D-panthenol.
Background technology
Panthenol is commonly called as pro-vitamin B
5, panthenol can be divided into DL body (DL-type), dextrorotatory form (D-type) and 3 kinds of forms of levo form (L-type), wherein has only the dextrorotatory form biologically active, and levo form does not have biological activity.D-panthenol has another name called Dexpanthenol, is a kind of steric isomer with opticity of panthenol, English name dexpanthenol; D-pantothenyl aleohol.
Dexpanthenol (D-panthenol) is the same effect thing of D-pantothenic acid; it is the precursor of coenzyme A; it is the important vitamines medicine; enter people's physical efficiency and be converted into pantothenic acid and then synthesize coenzyme A, promote the metabolism of human body protein, fat, carbohydrate, the mucous membrane and the gloss of protection skin surface; prophylactic generation; D-panthenol is widely used in medicine, food, cosmetic industry as nutritional supplement, concrete preparation such as oral liquid, collyrium, composite vitamin injection, shampoo, mousse, skin cream etc.
The synthetic method of D-panthenol is respectively in modern chemical industry (26), 2006, report among the 186-188, its preparation technology does under the condition of solvent for D-(-)-pantoyl lactone and 3-amino-1-propyl alcohol at ethanol, after the reacting by heating, concentrating under reduced pressure obtains D-panthenol, this technological reaction needs ethanol as solvent, because D-panthenol is a thick liquid, concentrating under reduced pressure usually can not be removed reaction solvent ethanol fully, and product colour is yellow simultaneously, optical value is on the low side, below requirement that all can not the fulfilling medicinal D-panthenol especially contains the injection of D-panthenol, and is higher to specification of quality such as its purity.
Summary of the invention
The purpose of this invention is to provide a kind of simple, economic and technical strong operability, method that productive rate is high prepares the high-optical-purity D-panthenol, total recovery is greater than 80%.
The preparation method of D-panthenol of the present invention, for D-(-)-pantoyl lactone and 3-amino-1-propyl alcohol react under solvent-free condition, obtain highly purified D-panthenol, described condition of no solvent refers to that reactant has only D-(-)-pantoyl lactone and 3-amino-1-propyl alcohol, does not contain other solvents arbitrarily.
D-(-)-pantoyl lactone can be made with extra care in advance, process for refining be D-(-)-pantoyl lactone through dissolution with solvents, and solvent crystallization purifying behind the activated carbon decolorizing, each step of process for refining can repeat 1～2 time.
In the process for refining of D-(-)-pantoyl lactone, the solvent of dissolving D-(-)-pantoyl lactone can be ethyl acetate, methylene dichloride, trichloromethane, acetone, methyl acetate etc., ethyl acetate.D-(-)-pantoyl lactone is 1: 1 to 1: 4 with the mass/volume ratio of the solvent of dissolving D-(-)-pantoyl lactone; Be preferably 1: 2.
In the process for refining of D-(-)-pantoyl lactone, the crystallization purification solvent is alkane solvents such as sherwood oil, hexanaphthene, normal heptane, normal hexane, preferred sherwood oil.D-(-)-pantoyl lactone is 1: 1 to 1: 8 with the mass/volume ratio of crystallization purification solvent; Be preferably 1: 4.
In the process for refining of D-(-)-pantoyl lactone, the decoloration active carbon consumption can be 0.01%～0.5% (w/v), the ratio of the weight that decoloration active carbon consumption w/v of the present invention refers to gac and decolouring total liquid volume refers to that as 0.1% the 1g gac joins in the solution that contains D-(-)-pantoyl lactone of 1 liter of volume altogether.
The preparation method of D-panthenol of the present invention, D-(-)-pantoyl lactone and 3-amino-1-propyl alcohol temperature of reaction is 40 ℃～100 ℃, preferred 50 ℃～70 ℃.
The preparation method of D-panthenol of the present invention, as: D-(-)-pantoyl lactone is joined in the reactor, add ethyl acetate, heated and stirred, the back of refluxing add 0.1% (w/v) activated carbon decolorizing half hour, filter, add the sherwood oil crystallization in the filtrate, filter, again D-(-)-pantoyl lactone is joined in the reactor, add ethyl acetate, heated and stirred, the back of refluxing adds activated carbon decolorizing half hour, filters, and adds the sherwood oil crystallization in the filtrate.Dry.With D-(-)-pantoyl lactone and the 3-amino-1-propyl alcohol reacting by heating 3h after handling, obtain the stickiness liquid of clear and bright colourless easy moisture absorption.
The present invention compared with prior art it is advantageous that: raw material is easy to get, the simple control easily of reaction process, do not use solvent in the reaction process, participate in reaction with 3-amino-1-propyl alcohol itself as solvent, reduced cost and environmental pollution, and the fine quality that improves product.
The quality controlling means of D-panthenol of the present invention can for:
This product is D-(2R)-2,4-dihydroxyl-N-(3-hydroxypropyl)-3,3-amide dimethyl butyrate.Calculate with anhydride, contain C
9H
19NO
4Should be 99.0%～101.0%.
[proterties] this product is colourless thick liquid, have draw moist.
This product is very easily dissolving in water, and is easily molten in methyl alcohol and ethanol, slightly soluble in ether.
It is an amount of that specific optical rotation is got this product, accurate claims surely, is dissolved in water and quantitatively is diluted to the solution that contains 50mg among every 1ml approximately, measures (two appendix VI of Chinese Pharmacopoeia version in 2005 E) in accordance with the law, and specific optical rotation should be+and 30.0 ° to+32.0 °.
The refractive index of refractive index this product (two appendix VI of Chinese Pharmacopoeia version in 2005 F) should be 1.495～1.502.
[discriminating] (1) this product infrared Absorption collection of illustrative plates should consistent with Dexpanthenol reference substance collection of illustrative plates (two appendix IV of Chinese Pharmacopoeia version in 2005 C).
(2) get the about 0.1g of this product, add water 1ml and make dissolving, add 5 of 1mol/L sodium hydroxide solution 5ml and copper sulfate test solutions, violent jolting should show mazarine.
(3) get the about 0.1g of this product, add water 10ml and make dissolving, get 1ml, add 1mol/L hydrochloric acid soln 1ml, heating is 30 minutes in water-bath, and cooling adds the 0.1g oxammonium hydrochloride, mix, add 1mol/L sodium hydroxide solution 5ml, placed 5 minutes, behind 1mol/L hydrochloric acid soln adjusting pH to 2.5～3.0, add 1 of iron trichloride test solution, answer displaing amaranth.
[inspection] potential of hydrogen is got this product 0.5g, add water 10ml dissolving after, measure (two appendix VIH of Chinese Pharmacopoeia version in 2005) in accordance with the law, the pH value must not be greater than 10.5.
The clarity of solution and color are got this product 1.0g, add water 20ml dissolving after, solution should be clarified colourless.
Related substance is got this product, be dissolved in water and dilute make contain Dexpanthenol 0.5mg among every 1ml approximately solution as need testing solution; Get need testing solution and quantitatively be diluted to the solution solution in contrast that contains 2.5 μ g among every 1ml approximately in right amount.Test according to high performance liquid chromatography (two appendix V of Chinese Pharmacopoeia version in 2005 D).With octadecylsilane chemically bonded silica is weighting agent, is moving phase with the 0.1% phosphoric acid solution-acetonitrile (95: 5) of 0.005mol/L sodium pentanesulfonate, and the detection wavelength is 210nm, and number of theoretical plate calculates by the Dexpanthenol peak should be not less than 1500.Get contrast solution 20 μ l and inject liquid chromatograph, regulate detection sensitivity, making the principal constituent peak-to-peak high is 20%～25% of full range; Get each 20 μ l of need testing solution and contrast solution more respectively and inject liquid chromatograph, the record color atlas is to 2 times of principal constituent peak retention time, in the need testing solution color atlas each impurity peak area and must not be greater than contrast solution main peak area (0.5%).
The 3-aminopropanol is got the about 1.0g of this product, the accurate title, decide, in the 50ml Erlenmeyer flask, after adding water 10ml dissolving, shake up, add 2 of bromothymol blue indicating liquids, use sulfuric acid titrating solution (0.01mol/L) titration to the solution displaing yellow, every 1ml sulfuric acid titrating solution (0.01mol/L) is equivalent to the aminopropanol of 0.75mg, must not cross 0.3%.
Moisture is got this product, measures according to aquametry (two appendix VIII of Chinese Pharmacopoeia version in 2005 M, the first method A), contains moisture and must not cross 0.5%.
Residue on ignition is got this product 1.0g, checks in accordance with the law and leaves over (two appendix VIII of Chinese Pharmacopoeia version in 2005 N) residue and must not cross 0.1%.
Heavy metal is got the residue of leaving under the residue on ignition item, checks to contain (two appendix VIII of Chinese Pharmacopoeia version in 2005 H, second method) heavy metal and must not cross 10/1000000ths in accordance with the law.
[assay] gets the about 0.4g of this product, the accurate title, decide, put in the 300ml flask, precision adds perchloric acid titrating solution (0.1mol/L) 50.0ml, refluxes 5 hours, cooling, notice preventing that moisture enters from prolong in the air that clean prolong with the 5ml Glacial acetic acid, washing lotion is incorporated flask into, add 5 of Viola crystallina indicating liquids, show blue-greenish colour with Potassium Hydrogen Phthalate solution titration to solution.And titrating result proofreaied and correct with blank test, every 1ml perchloric acid titration liquid (0.1mol/L) is equivalent to the C of 20.53mg
9H
19NO
4
The preparation precision of Potassium Hydrogen Phthalate solution takes by weighing the Potassium Hydrogen Phthalate of 20.42g in the 1000ml volumetric flask, adds warm the making fully of Glacial acetic acid and dissolves, and notes avoiding the moisture absorption.Be cooled to room temperature, be diluted to scale, shake up with Glacial acetic acid.
The D-panthenol of preparation of the present invention is tested by above-mentioned quality controlling means, and every quality control index all meets the requirements.
Embodiment
Following examples just are described more specifically the present invention, and the present invention is not limited in the content of following examples.
Embodiment 1
Getting D-(-)-pantoyl lactone 1.0kg, 3-amino-1-propyl alcohol 580g joins in the reactor, be heated to 50 ℃, reaction 3h, reduce to room temperature and promptly get the D-panthenol product, the stickiness liquid of clear and bright easy moisture absorption obtains finished product 1.58kg, product yield 100%, product is checked through above-mentioned quality controlling means, and every quality control index is all up to specification, and specific optical rotation is+30.0 °.
Embodiment 2
Take by weighing D-(-)-pantoyl lactone of 3kg, add the reactor heating of 10L; Measure the 6L ethyl acetate and add reactor, heated and stirred, the back of waiting to reflux adds gac 5g, decolours 30 minutes; Suction filtration, filtrate join in the 25L container, add sherwood oil 12L, mix under back 5 ℃ and leave standstill crystallization 2h; The suction filtration solid, 40 ℃ of vacuum-drying 2h of solid then, filtrate is reclaimed; Solid adds the 5L ethyl acetate, stirs reflux down, adds gac 5g, decolours 30 minutes; Filter, filtrate joins in the 25L container, adds sherwood oil 10L, mixes under back 5 ℃ and leaves standstill crystallization 2h; Suction filtration, 40 ℃ of vacuum-dryings of solid got white solid 2.7kg yield 90% in 10 hours then.D-(-)-pantoyl lactone 1.0kg, the 3-amino-1-propyl alcohol 580g that gets after making with extra care joins in the reactor, be heated to 50 ℃, reaction 3h, reduce to room temperature and promptly get the D-panthenol product, the stickiness liquid of clear and bright colourless easy moisture absorption obtains finished product 1.58kg, total yield of products 90%, product is checked through above-mentioned quality controlling means, and every quality control index is all up to specification, and specific optical rotation is+30.8 °.
Embodiment 3
Take by weighing D-(-)-pantoyl lactone of 3kg, add the reactor heating of 10L; Measure 6L acetone and add reactor, heated and stirred, the back of waiting to reflux adds gac 5g, decolours 30 minutes; Suction filtration, filtrate join in the 25L container, add sherwood oil 12L, mix under back 5 ℃ and leave standstill crystallization 2h; Suction filtration solid, 40 ℃ of vacuum-drying 2h of solid then; Solid adds 5L acetone, stirs reflux down, adds gac 5g, decolours 30 minutes; Filter, filtrate joins in the 25L container, adds sherwood oil 10L, mixes under back 5 ℃ and leaves standstill crystallization 2h; Suction filtration, 40 ℃ of vacuum-dryings of solid obtained white solid 2.6kg, yield 87% in 10 hours then.D-(-)-pantoyl lactone 1.0kg, the 3-amino-1-propyl alcohol 580g that gets after making with extra care joins in the reactor, is heated to 60 ℃, reaction 3h.Reduce to room temperature and promptly get the D-panthenol product, the stickiness liquid of clear and bright colourless easy moisture absorption obtains finished product 1.58kg, total yield of products 87%, and product is checked through above-mentioned quality controlling means, and every quality control index is all up to specification, and specific optical rotation is+30.6 °.
Embodiment 4
Take by weighing D-(-)-pantoyl lactone of 3kg, add the reactor heating of 10L; Measure the 6L ethyl acetate and add reactor, heated and stirred, the back of waiting to reflux adds gac 5g, decolours 30 minutes; Suction filtration, filtrate join in the 25L container, add normal hexane 12L, mix under back 5 ℃ and leave standstill crystallization 2h; The suction filtration solid, 40 ℃ of vacuum-drying 2h of solid then, filtrate is reclaimed; Solid adds the 5L ethyl acetate, stirs reflux down, adds gac 5g, decolours 30 minutes; Filter, filtrate joins in the 25L container, adds normal hexane 10L, mixes under back 5 ℃ and leaves standstill crystallization 2h; Suction filtration, 40 ℃ of vacuum-dryings of solid got white solid 2.6kg, yield 87% in 10 hours then.D-(-)-pantoyl lactone 1.0kg and the 3-amino-1-propyl alcohol 580g that get after making with extra care join in the reactor, are heated to 60 ℃, reaction 3h.Reduce to room temperature and promptly get the D-panthenol product, the stickiness liquid of clear and bright colourless easy moisture absorption obtains product 1.58kg, total yield of products 87%, and product is checked through above-mentioned quality controlling means, and every quality control index is all up to specification, and specific optical rotation is+30.8 °.
Embodiment 5
Take by weighing D-(-)-pantoyl lactone of 3kg, add the reactor heating of 10L; Measure the 6L methylene dichloride and add reactor, heated and stirred, the back of waiting to reflux adds gac 5g, decolours 30 minutes; Suction filtration, filtrate join in the 25L container, add normal hexane 12L, mix under back 5 ℃ and leave standstill crystallization 2h; The suction filtration solid, 40 ℃ of vacuum-drying 2h of solid then, filtrate is reclaimed; Solid adds the 5L methylene dichloride, stirs reflux down, adds gac 5g, decolours 30 minutes; Filter, filtrate joins in the 25L container, adds normal hexane 10L, mixes under back 5 ℃ and leaves standstill crystallization 2h; Suction filtration, 40 ℃ of vacuum-dryings of solid got white solid 2.5kg, yield 83% in 10 hours then.D-(-)-pantoyl lactone 1.0kg and the 3-amino-1-propyl alcohol 580g that get after making with extra care join in the reactor, are heated to 60 ℃, reaction 3h.Reduce to room temperature and promptly get the D-panthenol product, the stickiness liquid of clear and bright colourless easy moisture absorption obtains product 1.58kg, total yield of products 83%, and product is checked through above-mentioned quality controlling means, and every quality control index is all up to specification, and specific optical rotation is+30.5 °.
Embodiment 6
Take by weighing D-(-)-pantoyl lactone of 3kg, add the reactor heating of 10L; Measure the 6L methylene dichloride and add reactor, heated and stirred, the back of waiting to reflux adds gac 5g, decolours 30 minutes; Suction filtration, filtrate join in the 25L container, add hexanaphthene 12L, mix under back 5 ℃ and leave standstill crystallization 2h; The suction filtration solid, 40 ℃ of vacuum-drying 2h of solid then, filtrate is reclaimed; Solid adds the 5L methylene dichloride, stirs reflux down, adds gac 5g, decolours 30 minutes; Filter, filtrate joins in the 25L container, adds hexanaphthene 10L, mixes under back 5 ℃ and leaves standstill crystallization 2h; Suction filtration, 40 ℃ of vacuum-dryings of solid got white solid 2.5kg, yield 83% in 10 hours then.D-(-)-pantoyl lactone 1.0kg and the 3-amino-1-propyl alcohol 580g that get after making with extra care join in the reactor, are heated to 60 ℃, reaction 3h.Reduce to room temperature and promptly get the D-panthenol product, the stickiness liquid of clear and bright colourless easy moisture absorption obtains product 1.58kg, total yield of products 83%, and product is checked through above-mentioned quality controlling means, and every quality control index is all up to specification, and specific optical rotation is+30.6 °.
Embodiment 7
Take by weighing D-(-)-pantoyl lactone of 3kg, add the reactor heating of 10L; Measure the 6L ethyl acetate and add reactor, heated and stirred, the back of waiting to reflux adds gac 20g, decolours 30 minutes; Suction filtration, filtrate join in the 25L container, add sherwood oil 12L, mix under back 5 ℃ and leave standstill crystallization 2h; The suction filtration solid, 40 ℃ of vacuum-drying 2h of solid then, filtrate is reclaimed; Solid adds the 5L ethyl acetate, stirs reflux down, adds gac 20g, decolours 30 minutes; Filter, filtrate joins in the 25L container, adds sherwood oil 10L, mixes under back 5 ℃ and leaves standstill crystallization 2h; Suction filtration, 40 ℃ of vacuum-dryings of solid got white solid 2.5kg yield 83% in 10 hours then.D-(-)-pantoyl lactone 1.0kg, the 3-amino-1-propyl alcohol 580g that gets after making with extra care joins in the reactor, be heated to 50 ℃, reaction 3h, reduce to room temperature and promptly get the D-panthenol product, the stickiness liquid of clear and bright colourless easy moisture absorption obtains finished product 1.58kg, total yield of products 83%, product is checked through above-mentioned quality controlling means, and every quality control index is all up to specification, and specific optical rotation is+30.3 °.
Embodiment 8
Take by weighing D-(-)-pantoyl lactone of 3kg, add the reactor heating of 10L; Measure the 6L ethyl acetate and add reactor, heated and stirred, the back of waiting to reflux adds gac 1g, decolours 30 minutes; Suction filtration, filtrate join in the 25L container, add sherwood oil 12L, mix under back 5 ℃ and leave standstill crystallization 2h; The suction filtration solid, 40 ℃ of vacuum-drying 2h of solid then, filtrate is reclaimed; Solid adds the 5L ethyl acetate, stirs reflux down, adds gac 1g, decolours 30 minutes; Filter, filtrate joins in the 25L container, adds sherwood oil 10L, mixes under back 5 ℃ and leaves standstill crystallization 2h; Suction filtration, 40 ℃ of vacuum-dryings of solid got white solid 2.7kg yield 90% in 10 hours then.D-(-)-pantoyl lactone 1.0kg, the 3-amino-1-propyl alcohol 580g that gets after making with extra care joins in the reactor, be heated to 50 ℃, reaction 3h, reduce to room temperature and promptly get the D-panthenol product, the stickiness liquid of clear and bright colourless easy moisture absorption obtains finished product 1.58kg, total yield of products 90%, product is checked through above-mentioned quality controlling means, and every quality control index is all up to specification, and specific optical rotation is+30.5 °.
Embodiment 9
Take by weighing D-(-)-pantoyl lactone of 3kg, add the reactor heating of 10L; Measure the 6L ethyl acetate and add reactor, heated and stirred, the back of waiting to reflux adds gac 5g, decolours 30 minutes; Suction filtration, filtrate join in the 25L container, add sherwood oil 12L, mix under back 5 ℃ and leave standstill crystallization 2h; The suction filtration solid, 40 ℃ of vacuum-dryings of solid got white solid 2.8kg yield 93% in 10 hours then.D-(-)-pantoyl lactone 1.0kg, the 3-amino-1-propyl alcohol 580g that gets after making with extra care joins in the reactor, be heated to 50 ℃, reaction 3h, reduce to room temperature and promptly get the D-panthenol product, the stickiness liquid of clear and bright colourless easy moisture absorption obtains finished product 1.58kg, total yield of products 93%, product is checked through above-mentioned quality controlling means, and every quality control index is all up to specification, and specific optical rotation is+30.2 °.
Embodiment 10
Take by weighing D-(-)-pantoyl lactone of 3kg, add the reactor heating of 10L; Measure 6L acetone and add reactor, heated and stirred, the back of waiting to reflux adds gac 5g, decolours 30 minutes; Suction filtration, filtrate join in the 25L container, add sherwood oil 12L, mix under back 5 ℃ and leave standstill crystallization 2h; The suction filtration solid, 40 ℃ of vacuum-dryings of solid got white solid 2.8kg yield 93% in 10 hours then.D-(-)-pantoyl lactone 1.0kg, the 3-amino-1-propyl alcohol 580g that gets after making with extra care joins in the reactor, be heated to 50 ℃, reaction 3h, reduce to room temperature and promptly get the D-panthenol product, the stickiness liquid of clear and bright colourless easy moisture absorption obtains finished product 1.58kg, total yield of products 93%, product is checked through above-mentioned quality controlling means, and every quality control index is all up to specification, and specific optical rotation is+30.2 °.
Embodiment 11
Get D-(-)-pantoyl lactone 1.0kg, 3-amino-1-propyl alcohol 580g and join in the reactor, measure 6L ethanol and add in the reactor, be heated to 50 ℃, reaction 3h adds gac 1g, decolours 30 minutes, suction filtration, filtrate decompression concentrates removes ethanol, gets the stickiness liquid of faint yellow easy moisture absorption, obtains finished product 1.58kg, product yield 100%, product is checked through above-mentioned quality controlling means, and specific optical rotation is+29.1 °, 3-aminopropanol 0.9%.
Claims (8)
1. the preparation method of a D-panthenol is characterized in that D-(-)-pantoyl lactone and 3-amino-1-propyl alcohol reacts, and obtains D-panthenol under solvent-free condition.
2. the preparation method of D-panthenol as claimed in claim 1 is characterized in that D-(-)-pantoyl lactone makes with extra care in advance, process for refining be D-(-)-pantoyl lactone through dissolution with solvents, and solvent crystallization purifying behind the activated carbon decolorizing.
3. the process for purification of D-as claimed in claim 2 (-)-pantoyl lactone, the solvent of dissolving D-(-)-pantoyl lactone is ethyl acetate, methylene dichloride, trichloromethane, acetone, methyl acetate etc., ethyl acetate.
4. the process for purification of D-as claimed in claim 2 (-)-pantoyl lactone, crystallization purification solvent are alkane solvents such as sherwood oil, hexanaphthene, normal heptane, normal hexane, preferred sherwood oil.
5. the process for purification of D-as claimed in claim 2 (-)-pantoyl lactone is characterized in that D-(-)-pantoyl lactone and the mass/volume ratio of the solvent of dissolving D-(-)-pantoyl lactone are 1: 1 to 1: 4, is preferably 1: 2.
6. the process for purification of D-as claimed in claim 2 (-)-pantoyl lactone is characterized in that D-(-)-pantoyl lactone and the mass/volume ratio of crystallization purification solvent are 1: 1 to 1: 8, is preferably 1: 4.
7. the process for purification of D-as claimed in claim 2 (-)-pantoyl lactone is characterized in that the decoloration active carbon consumption is 0.01%～0.5% (w/v).
8. the preparation method of D-panthenol as claimed in claim 1, D-(-)-pantoyl lactone and 3-amino-1-propyl alcohol temperature of reaction is 40 ℃～100 ℃, preferred 50 ℃～70 ℃.
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| CN110028416A (en) * | 2019-04-29 | 2019-07-19 | 安徽安力肽生物科技有限公司 | The preparation method of DL-panthenol |
| CN110835309A (en) * | 2019-11-28 | 2020-02-25 | 安徽泰格生物科技有限公司 | Crystallization method of DL-panthenol |
| CN112047851A (en) * | 2020-08-20 | 2020-12-08 | 山东新和成精化科技有限公司 | Preparation method of D-panthenol |
| CN112174845A (en) * | 2020-09-27 | 2021-01-05 | 安徽泰格生物科技有限公司 | Preparation method of D-panthenol |
| CN112409303A (en) * | 2020-12-09 | 2021-02-26 | 合肥工业大学 | Purification method of D-pantoic acid lactone |
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| RU2667652C2 (en) * | 2014-04-03 | 2018-09-21 | Пола Кемикал Индастриз, Инк. | Melanogenesis inhibitor, which contains d-pantotenyl alcohol and cosmetic means for skin bleaching that contains such melanogenesis inhibitor |
| US10568822B2 (en) | 2014-04-03 | 2020-02-25 | Pola Chemical Industries, Inc. | Melanogenesis inhibitor comprising d-pantothenyl alcohol, and skin-whitening cosmetic containing same melanogenesis inhibitor |
| CN110028416A (en) * | 2019-04-29 | 2019-07-19 | 安徽安力肽生物科技有限公司 | The preparation method of DL-panthenol |
| CN110835309A (en) * | 2019-11-28 | 2020-02-25 | 安徽泰格生物科技有限公司 | Crystallization method of DL-panthenol |
| CN112047851A (en) * | 2020-08-20 | 2020-12-08 | 山东新和成精化科技有限公司 | Preparation method of D-panthenol |
| CN112047851B (en) * | 2020-08-20 | 2023-04-11 | 山东新和成精化科技有限公司 | Preparation method of D-panthenol |
| CN112174845A (en) * | 2020-09-27 | 2021-01-05 | 安徽泰格生物科技有限公司 | Preparation method of D-panthenol |
| CN112174845B (en) * | 2020-09-27 | 2024-01-12 | 安徽泰格生物科技有限公司 | Preparation method of D-panthenol |
| CN112409303A (en) * | 2020-12-09 | 2021-02-26 | 合肥工业大学 | Purification method of D-pantoic acid lactone |
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