CN107488143B - Nicotinamide and preparation method thereof - Google Patents
Nicotinamide and preparation method thereof Download PDFInfo
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- CN107488143B CN107488143B CN201710706089.7A CN201710706089A CN107488143B CN 107488143 B CN107488143 B CN 107488143B CN 201710706089 A CN201710706089 A CN 201710706089A CN 107488143 B CN107488143 B CN 107488143B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
Abstract
The invention provides nicotinamide with low content of nicotinic acid, which is characterized in that the content of nicotinic acid in the nicotinamide is lower than 190ppm, preferably lower than 150ppm, preferably lower than 100ppm, preferably lower than 80ppm, preferably lower than 40 ppm. The invention also provides a preparation method for preparing nicotinamide, which is characterized by comprising the following steps: a) mixing nicotinamide with water and/or ethanol in a weight to volume ratio (g/ml) of 1: 0.5-5, preferably 1: 1-4, more preferably 1: 1-2; b) dropwise adding or not adding 1-10 wt% of alkaline solution until the pH value of the reaction system is 6-9; the concentration of the alkaline solution is preferably 3 to 8% by weight, more preferably 4 to 6% by weight; the pH value of the reaction system is preferably 6.5-7.5; c) stirring for 0.5 to 5 hours, preferably 1 to 3 hours, more preferably 1 to 2 hours; d) filtering, collecting solid and drying. The nicotinic acid content of the nicotinamide provided by the invention is very low. The preparation method provided by the invention has the advantages of simple steps, no special requirements on production equipment, environmental friendliness and low production cost.
Description
Technical Field
The invention relates to nicotinamide and a preparation method thereof, in particular to nicotinamide with low nicotinic acid content and a preparation method thereof.
Background
Niacinamide and niacin are collectively referred to as vitamin PP. Nicotinic acid is converted in the human body to nicotinamide, which is the precursor of coenzyme I (nicotinamide adenine dinucleotide, NAD) and coenzyme II (nicotinamide adenosine dinucleotide phosphate, NADP). Niacinamide is able to penetrate into human skin. After topical application of niacinamide, the levels of coenzyme I in skin cells increased, which is evidence of transdermal absorption. Nicotinamide, a precursor of the NADP family of coenzymes, exerts a significant effect on skin improvement in 6 aspects (BissettDL, Obbing JE, Saud A, et al. clinical niacinamide precursors binding and applying platelet binding resins 2003,32S: 9-18): (1) oxidation resistance; (2) epidermal barrier function, which is improved with the improvement of keratinocyte differentiation after external application of niacinamide. Meanwhile, the improvement of the barrier function is also shown in that the loss of epidermal water is reduced and the water of the horny layer is increased, namely, the moisturizing capability is improved; (3) improving erythema and mottle; (4) inhibiting skin yellowing, the external niacinamide acts to inhibit oxidation processes such as oxidation of proteins, glycosylation and Maillard reaction (increase of oxidation products of collagen in human skin increases 5 times from 20 to 80 years), thereby inhibiting skin yellowing; (5) fine lines and wrinkles, niacinamide elevating the levels of the epidermal keratin, filaggrin and involucrin, increasing the production of dermal matrix collagen; (6) pigmentation: topical niacinamide is effective in reducing epidermal pigmentation and reducing pigmented spots.
Clinical studies of nicotinamide also gave good results. Tanno et al (Tanno O, Ota Y, Kitamura N, et al, Nicotinamide derivatives biology of ceramides as well as other stratumcoenema lipids to immunological skin metabolism [ J ]. Br J Dermatol.2000,143: 524-. After eight weeks of treatment, the pigmentation on the side with niacinamide became visibly bright white (P < 0.05).
A human body test is carried out on the back of a hand by using a multi-angle reflection spectrophotometer, and the skin surface structure is smooth by using nicotinamide externally, so that a good effect is produced. Long-term application of 2.5% niacinamide can correct skin surface damage due to aging (p < 0.05). The 3.5% niacinamide cream used for four weeks, the roughness of the skin was reduced by 14.8% (P ═ 0.05) compared to placebo. In one study, 50 white women with clinical signs of photodamage, face was half each with 5% niacinamide and vehicle control 2 times daily for 12 weeks. The skin appearance of topical niacinamide exhibits various improvements including reduction of fine lines and wrinkles, improvement of pigmentation spots, red spots, sallowness of the skin and improvement of skin elasticity.
Nicotinic acid interacts with receptors in the skin and has a drug-conditioning effect on skin superior to niacinamide. However, nicotinic acid receptors are G-protein coupled receptors and stimulation leads to peripheral vasodilation, resulting in a flushing response in the skin. Most users strongly reject this.
In order to reduce the irritation of niacin as much as possible, the content of niacin in niacinamide used in cosmetics must be sufficiently low. The concentration of nicotinic acid in currently marketed nicotinamide is relatively high, for example, the content of nicotinic acid is about 6000-8000ppm, so how to reduce nicotinic acid in nicotinamide becomes especially important.
In US patent US3678060, nicotinic acid is removed by a resin method, but the process is complicated and uneconomical.
SUMMARY OF THE PATENT FOR INVENTION
In order to reduce the irritation of niacinamide products to the skin, one aspect of the present invention provides niacinamide with a low level of niacin.
On the other hand, the invention provides a method for preparing nicotinamide with low nicotinic acid content, which has simple process and low cost.
To this end, the present invention provides a nicotinamide characterized in that the nicotinic acid content of the nicotinamide is below 190ppm, preferably below 150ppm, preferably below 100ppm, preferably below 80ppm, preferably below 40 ppm.
The invention also provides nicotinamide, which is characterized in that the content of nicotinic acid in the nicotinamide is less than 800ppm, preferably less than 100ppm, and the nicotinamide is obtained by the following steps:
a) mixing nicotinamide with water and/or ethanol in a weight to volume ratio (g/ml) of 1: 0.5-5, preferably 1: 1-4, more preferably 1: 1-2;
b) dropwise adding or not adding 1-10 wt% of alkaline solution until the pH value of the reaction system is 6-9; the concentration of the alkaline solution is preferably 3 to 8% by weight, more preferably 4 to 6% by weight; the pH value of the reaction system is preferably 6.5-7.5;
c) stirring for 0.5 to 5 hours, preferably 1 to 3 hours, more preferably 1 to 2 hours;
d) filtering, collecting solid and drying.
The invention also provides a preparation method for preparing nicotinamide, which is characterized by comprising the following steps:
a) mixing nicotinamide with water and/or ethanol in a weight to volume ratio (g/ml) of 1: 0.5-5, preferably 1: 1-4, more preferably 1: 1-2;
b) dropwise adding or not adding 1-10 wt% of alkaline solution until the pH value of the reaction system is 6-9; the concentration of the alkaline solution is preferably 3 to 8% by weight, more preferably 4 to 6% by weight; the pH value of the reaction system is preferably 6.5-7.5;
c) stirring for 0.5 to 5 hours, preferably 1 to 3 hours, more preferably 1 to 2 hours;
d) filtering, collecting solid and drying.
The nicotinamide provided by the invention has low nicotinic acid content, is favorable for reducing the irritation of nicotinic acid to skin, expands the application range of the nicotinamide, correspondingly improves the concentration of the nicotinamide and provides more reliable guarantee for preparing cosmetics containing the nicotinamide.
In the research of preparing nicotinamide with low nicotinic acid content, the inventor of the present application has conducted a great deal of experiments, and adopted various parameters such as various solvents and temperatures, and has surprisingly found that unexpected effects can be obtained by adopting a solvent which is easily soluble in nicotinamide, and controlling the parameters such as the amount of the solvent and the pH value of the reaction system, for example, nicotinamide with nicotinic acid content of about 6500ppm is reduced to less than 800ppm, even to dozens of ppm, and the yield is good, and the effects are very significant.
The preparation method of nicotinamide provided by the invention has the advantages of simple steps, no special requirements on production equipment, environmental friendliness and low production cost.
Drawings
Figure 1 is an HPLC diagram for detection of nicotinamide starting material.
Figure 2 is an HPLC profile of nicotinamide prepared in example 1.
Detailed Description
The invention provides nicotinamide, which is characterized in that the content of nicotinic acid in the nicotinamide is less than 190ppm, preferably less than, for example, 180ppm, 170ppm and 160 ppm; more preferably, less than, for example, 150ppm, 140ppm, 130ppm, 120ppm, 110 ppm; most preferably below, e.g., 100ppm, 80ppm, 60ppm, 40 ppm. The present inventors have surprisingly prepared a nicotinamide with a low niacin content, which will greatly expand the range of applications of nicotinamide.
The invention also provides nicotinamide, which is characterized in that the content of nicotinic acid in the nicotinamide is less than 800ppm, preferably less than 500 ppm; and said nicotinamide is obtained by the following steps:
a) mixing nicotinamide with water and/or ethanol in a weight to volume ratio (g/ml) of 1: 0.5-5, preferably 1: 1-4, more preferably 1: 1-2;
b) dropwise adding or not adding 1-10 wt% of alkaline solution until the pH value of the reaction system is 6-9; the concentration of the alkaline solution is preferably 3 to 8% by weight, more preferably 4 to 6% by weight; the pH value of the reaction system is preferably 6.5-7.5;
c) stirring for 0.5 to 5 hours, preferably 1 to 3 hours, more preferably 1 to 2 hours;
d) filtering, collecting solid and drying.
As a preferred embodiment, the nicotinamide has a nicotinic acid content of less than 200ppm, wherein, in step a), nicotinamide and ethanol are mixed in a weight to volume ratio (g/ml) of 1: 1-2, mixing; in step b), no alkaline solution is added dropwise; in step c), stirring at room temperature for 1-2 hours; repeating steps a) and c); for this embodiment, steps a) and c) may be repeated one or more times, depending on the niacin content of the niacinamide.
As a preferred embodiment, the nicotinamide has a nicotinic acid content of less than 200ppm, wherein, in step a), nicotinamide and ethanol are mixed in a weight to volume ratio (g/ml) of 1: 1-2, mixing; in the step b), 4-6 wt% of alkaline solution is dripped until the pH value of the reaction system is 6.5-7.5; in step c), stirring is carried out at room temperature for 1 to 2 hours.
As a preferred embodiment, the nicotinamide has a nicotinic acid content of less than 100ppm, preferably less than 80ppm, preferably less than 40ppm, wherein, in step a), nicotinamide and ethanol are present in a weight to volume ratio (g/ml) of 1: 1-2, mixing, and heating to reflux; in the step b), 4-6 wt% of alkaline solution is dripped until the pH value of the reaction system is 6.5-7.5; in the step c), stirring for 1-2 hours under the condition of heat preservation, and cooling to room temperature; in order to further reduce the content of nicotinic acid in nicotinamide, the ethanol is preferably anhydrous ethanol.
The alkaline solution may be an alkaline solution in the usual sense, such as various strong bases, weak bases, alkaline salts, and the like; as a preferred embodiment, the alkaline solution is a sodium hydroxide solution and/or a potassium hydroxide solution, preferably a sodium hydroxide alcoholic solution and/or a potassium hydroxide alcoholic solution.
In order to further reduce the content of nicotinic acid in nicotinamide, as a preferred embodiment, the nicotinamide raw material may be subjected to a grinding treatment.
In order to further reduce the content of nicotinic acid in nicotinamide, as a preferred embodiment, the collected solid is washed one or more times, and the solvent may be selected to be a nicotinic acid-compatible solvent.
The invention also provides a preparation method for preparing nicotinamide, which is characterized by comprising the following steps:
a) mixing nicotinamide with water and/or ethanol in a weight to volume ratio (g/ml) of 1: 0.5-5, preferably 1: 1-4, more preferably 1: 1-2;
b) dropwise adding or not adding 1-10 wt% of alkaline solution until the pH value of the reaction system is 6-9; the concentration of the alkaline solution is preferably 3 to 8% by weight, more preferably 4 to 6% by weight; the pH value of the reaction system is preferably 6.5-7.5;
c) stirring for 0.5 to 5 hours, preferably 1 to 3 hours, more preferably 1 to 2 hours;
d) filtering, collecting solid and drying.
As a preferred embodiment, wherein, in step a), nicotinamide and ethanol are mixed in a weight to volume ratio (g/ml) of 1: 1-2, mixing; alkaline solution is not dripped; in step c), stirring at room temperature for 1-2 hours; repeating steps a) and c); for this embodiment, steps a) and c) may be repeated one or more times, depending on the niacin content of the niacinamide.
As a preferred embodiment, wherein, in step a), nicotinamide and ethanol are mixed in a weight to volume ratio (g/ml) of 1: 1-2, mixing; in the step b), 4-6 wt% of alkaline solution is dripped until the pH value of the reaction system is 6.5-7.5; in step c), stirring is carried out at room temperature for 1 to 2 hours.
As a preferred embodiment, wherein, in step a), nicotinamide and ethanol are mixed in a weight to volume ratio (g/ml) of 1: 1-2, mixing, and heating to reflux; in the step b), 4-6 wt% of alkaline solution is dripped until the pH value of the reaction system is 6.5-7.5; in the step c), stirring for 1-2 hours under the condition of heat preservation, and cooling to room temperature; in order to further reduce the content of nicotinic acid in nicotinamide, the ethanol is preferably anhydrous ethanol.
The alkaline solution may be an alkaline solution in the usual sense, such as various strong bases, weak bases, alkaline salts, and the like; as a preferred embodiment, the alkaline solution is a sodium hydroxide solution and/or a potassium hydroxide solution, preferably a sodium hydroxide alcoholic solution and/or a potassium hydroxide alcoholic solution.
In order to further reduce the content of nicotinic acid in nicotinamide, as a preferred embodiment, the nicotinamide raw material may be subjected to a grinding treatment in advance.
To further reduce the niacin content of the niacinamide, the collected solids are washed one or more times as a preferred embodiment.
Examples
HPLC detection conditions
A chromatographic column: HYPERSIL ODS-2,5 μm,250mm x 46mm
Column temperature: 23 deg.C
Mobile phase: methanol: acetonitrile: water ═ 20:20:60(V/V)
Flow rate: 0.8ml/min
Detection wavelength: 216nm
Sample introduction amount: 20 μ l
Calculating the content of the nicotinic acid:
the content of nicotinic acid in the sample to be detected is calculated according to the following formula:
Cnicotinic acid/CSign board=[ADetection of/CDetection of]/[ATo pair/CTo pair]
CNicotinic acid=[ADetection of/CDetection of]/[ATo pair/CTo pair]*CSign board
Description of the symbols in the formula:
Cnicotinic acidThe content (w/w; ppm) of nicotinic acid in the sample
CSign boardContent of reference Standard (%, w/w)
ADetection ofPeak area of nicotinic acid in test sample
CDetection ofConcentration of nicotinic acid in test sample
ATo pairPeak area of nicotinic acid control
CTo pairConcentration of nicotinic acid control
Example 1
10g of nicotinamide (6500 ppm of nicotinic acid content detected by HPLC, Beijing Beili Lai Si biochemicals Co., Ltd.) and 20ml of absolute ethyl alcohol are stirred and heated to reflux, 5% of potassium hydroxide solution of the absolute ethyl alcohol is dripped until the pH value is about 7, the nicotinamide is completely dissolved, the temperature is kept for 1 hour, the mixture is cooled to the room temperature, the nicotinamide is separated out, filtered, and the solid is collected and dried. HPLC detection is adopted, the nicotinic acid content in the nicotinamide is 32ppm, and the yield is 84%.
Example 2
10g of nicotinamide (6500 ppm of nicotinic acid content detected by HPLC, Beijing Beili Lai Si biochemicals Co., Ltd.) and 30ml of ethanol are stirred and heated to reflux, 3% sodium hydroxide aqueous solution is dripped until the pH value is about 7.5, the nicotinamide is completely dissolved, the temperature is kept for 2 hours, the mixture is cooled to room temperature, the nicotinamide is separated out, and the solid is collected and dried. HPLC detection is adopted, the nicotinic acid content in the nicotinamide is 84ppm, and the yield is 80%.
Example 3
Nicotinamide (6500 ppm nicotinic acid content by HPLC, Beijing Bellais biochemistry Ltd.) 10g, ethanol 40ml, stirring at room temperature for 4 hours, filtering, collecting solid, and drying. HPLC detection is adopted, the nicotinic acid content in the nicotinamide is 300ppm, and the yield is 82%.
Example 4
Nicotinamide (6500 ppm nicotinic acid content by HPLC, Beijing Bellais biochemistry Ltd.) 10g, ethanol 10ml, stirring at room temperature for 4 hours, filtering, collecting solid, and drying. Repeating the steps for 1 time, and detecting by adopting HPLC, wherein the nicotinic acid content in the nicotinamide is 190ppm, and the yield is 80%.
Example 5
10g of nicotinamide (6500 ppm of nicotinic acid content detected by HPLC, Beijing Beili Lai Si biochemicals Co., Ltd.) and 15ml of ethanol are added dropwise with 5% potassium hydroxide ethanol solution at room temperature until the pH value is about 6.5, stirring is continued for 1 hour, HPLC is adopted for detection, the nicotinic acid content in the nicotinamide is 170ppm, and the yield is 81%.
Example 6
10g of nicotinamide (6500 ppm of nicotinic acid content detected by HPLC, Beijing Bellais biochemistry Co., Ltd.) and 5ml of water are added dropwise into 6% sodium hydroxide aqueous solution at room temperature until the pH value is about 8, stirring is continued for 1 hour, and HPLC is adopted for detection, so that the nicotinic acid content in the nicotinamide is 800ppm, and the yield is 60%.
Example 7
10g of nicotinamide (6500 ppm of nicotinic acid content detected by HPLC, Beijing Beili Lai Si biochemicals Co., Ltd.) and 8ml of water are added dropwise into the mixture at room temperature until the pH value reaches about 9, the mixture is continuously stirred for 1 hour, and the content of the nicotinic acid in the nicotinamide is 440ppm and the yield is 70% by HPLC detection.
Claims (10)
1. A preparation method of nicotinamide, which is characterized by comprising the following steps:
a) mixing nicotinamide and ethanol in a weight-volume ratio of 1: 0.5-5 mixing;
b) dropwise adding 1-10 wt% of alkaline solution to the reaction system until the pH value is 6.5-7.5, wherein the alkaline solution is sodium hydroxide alcoholic solution and/or potassium hydroxide alcoholic solution;
c) stirring for 0.5-5 hours;
d) filtering, collecting solid and drying.
2. The method of claim 1, wherein in step a), the weight-to-volume ratio of nicotinamide to ethanol is 1: 1-4, and mixing.
3. The method of claim 1, wherein in step a), the weight-to-volume ratio of nicotinamide to ethanol is 1: 1-2, and mixing.
4. The method according to claim 1, wherein the concentration of the alkaline solution in step b) is 3 to 8 wt.%.
5. The method according to claim 1, wherein the concentration of the alkaline solution in step b) is 4 to 6 wt%.
6. The method according to claim 1, wherein in step c), the mixture is stirred for 1 to 3 hours.
7. The method according to claim 1, wherein in step c), the mixture is stirred for 1 to 2 hours.
8. The method of claim 1, wherein in step a), the weight-to-volume ratio of nicotinamide to ethanol is 1: 1-2, mixing; in step b), the concentration of the alkaline solution is 4 to 6 wt% in step c), stirring at room temperature for 1 to 2 hours.
9. The method of claim 1, wherein in step a), the weight-to-volume ratio of nicotinamide to ethanol is 1: 1-2, mixing, and heating to reflux; in step b), the concentration of the alkaline solution is 4-6 wt%; in step c), stirring for 1-2 hours under heat preservation, and cooling to room temperature.
10. The method according to claim 9, wherein the ethanol is absolute ethanol.
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2496114A (en) * | 1945-10-08 | 1950-01-31 | Scherer Corp R P | Purification of nicotinamide |
US4447615A (en) * | 1980-07-30 | 1984-05-08 | Degussa Aktiengesellschaft | Process for the purification of nicotinic acid amide I |
CN104496894A (en) * | 2014-11-22 | 2015-04-08 | 安徽国星生物化学有限公司 | Preparation method of high purity nicotinamide and nicotinic acid |
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JPS49100087A (en) * | 1973-01-29 | 1974-09-20 |
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Publication number | Priority date | Publication date | Assignee | Title |
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US2496114A (en) * | 1945-10-08 | 1950-01-31 | Scherer Corp R P | Purification of nicotinamide |
US4447615A (en) * | 1980-07-30 | 1984-05-08 | Degussa Aktiengesellschaft | Process for the purification of nicotinic acid amide I |
CN104496894A (en) * | 2014-11-22 | 2015-04-08 | 安徽国星生物化学有限公司 | Preparation method of high purity nicotinamide and nicotinic acid |
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