CN110467691A - A method of preparing acetylation hyaluronic acid - Google Patents
A method of preparing acetylation hyaluronic acid Download PDFInfo
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- CN110467691A CN110467691A CN201910900142.6A CN201910900142A CN110467691A CN 110467691 A CN110467691 A CN 110467691A CN 201910900142 A CN201910900142 A CN 201910900142A CN 110467691 A CN110467691 A CN 110467691A
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- sodium hyaluronate
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
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Abstract
The invention discloses a kind of methods for preparing acetylation hyaluronic acid, including, following steps: S1, prepares material: preparing formamide solvent, Sodium Hyaluronate and the acetic anhydride of different volumes；S2, dissolution: the formamide solvent prepared in S1 is placed into a container, then the Sodium Hyaluronate prepared in S1 is scattered in the container containing formamide solvent, is dissolved；S3, addition: the acetic anhydride in S1 is added in S2 containing in Sodium Hyaluronate and formamide solvent container；S4, stirring: Sodium Hyaluronate, formamide solvent and the acetic anhydride in S3 container are discharged into the inside of blender again.It is related to technical field of biochemical industry.The method of the preparation acetylation hyaluronic acid, not only technique is simple and direct, convenient for making, and high income, production cost greatly reduces, and small to molecule extent of the destruction, the water conservation moistening effect of original Sodium Hyaluronate will be substantially improved after addition acetyl group.
Description
Technical field
The present invention relates to technical field of biochemical industry, specially a kind of method for preparing acetylation hyaluronic acid.
Background technique
Sodium Hyaluronate also known as sodium hyaluronate are made of more the disaccharide recurring unit of glucuronic acid and aminoglucose
Sugar is distributed widely in the connective tissues such as skin, vitreum, umbilical cord, cartilage, knuckle synovia, and plays moisturizing, battalion wherein
The physiological actions such as feeding, reparation and pre- antisitic defect；By adding acetyl group in hyaluronic acid structure, bioactivity difference is bright
Aobvious, solution has good open-minded elasticity and moisturizing, lubricating function, is widely used in cosmetics moisturizing beauty, ophthalmologic operation firewood bullet
The lubricant of agent and Bones and joints lubrication, moisture retention substantially enhances, and is easier to be absorbed by the body.The outer used time can be absorbed by the skin, and increase
Add the content of subcutaneous tissue, skin elasticity can be effectively increased, achieve the effect that deep moisturizing, it is oral to supplement intracorporal deficiency,
To beauty, osteoarthritis is prevented and treated with obvious action, has become the hot spot of research at present.
Acetylation hyaluronic acid has the function of inhibiting tumour cell diffusion and promotes angiogenesis, recent research indicate that also
Immune activation effect, promotion ostosis effect and drug targeting effect with cell.Acetylation hyaluronic acid is in medicine, guarantor
Good application prospect is presented in terms of strong product, however the preparation method of the Sodium Hyaluronate of acetylation at present has certain lack
Point, such as this method have used a large amount of water when washing acetylation hyaluronic acid after acetylization reaction, in precipitating,
A large amount of acetone has been used, then product has been dehydrated using a large amount of dehydrated alcohol again, so that consuming largely has
Solvent, production stage is complicated, and the production cycle is long and unfriendly to environment, is unfavorable for industrialized production.
Summary of the invention
(1) the technical issues of solving
In view of the deficiencies of the prior art, the present invention provides a kind of methods for preparing acetylation hyaluronic acid, solve production step
Rapid problem complicated, yield is low.
(2) technical solution
In order to achieve the above object, the present invention is achieved by the following technical programs: a kind of side preparing acetylation hyaluronic acid
Method includes following steps:
S1, prepare material: preparing formamide solvent, Sodium Hyaluronate and the acetic anhydride of different volumes；
S2, dissolution: the formamide solvent prepared in S1 is placed into a container, then the Sodium Hyaluronate prepared in S1 is divided
It dissipates and is placed into the container containing formamide solvent, dissolved；
S3, addition: the acetic anhydride in S1 is added in S2 containing in Sodium Hyaluronate and formamide solvent container；
S4, stirring: Sodium Hyaluronate, formamide solvent and the acetic anhydride in S3 container are discharged into the inside of blender again, passed through
Blender is stirred and reacts to Sodium Hyaluronate, formamide solvent and acetic anhydride, forms new product；
The Sodium Hyaluronate, formamide solvent and the acetic anhydride that stir inside blender in S4: being stirred by S5, precipitating again and instead
Formed new product is answered to carry out precipitation process；
The product precipitated in S5: being placed into the inside of washing facility by S6, washing again, the production by washing facility to precipitating in S5
Object carries out washing filtration treatment；
The product of carrying out washing treatment in S5: being finally placed into the inside of spray drying machine by S7, spray drying, by spray drying machine to washup in S5
The product of reason carries out spray drying processing and is being cooled down after spray drying processing, obtaining acetylation hyaluronic acid.
Further, formamide solvent and acetic anhydride mixing in acetic anhydride the final concentration 5%-10%, the S1 in the S1
The ratio of solvent is 2:4；And the ratio of hyaluronic acid and formamide solvent and acetic anhydride summation is 1.5:20-55.
Further, the Sodium Hyaluronate in the S1 is solid powdery.
Further, the formamide solvent in the S1 is organic formamide solvent.
Further, acetic anhydride addition is contained into S2 Sodium Hyaluronate and formamide solvent container in the S3, needed
It to be operated simultaneously under acidic environment, carry out acetylization reaction, and acylation reaction temperature is 10-30 DEG C, when reaction solution is transparent
.
Further, in the S4 stirring of blender time 10-20min.
Further, the sedimentation time in the S5 is 30-45min.
Further, the temperature inside the spray drying machine in the S7 is 200 DEG C -300 DEG C, and the spray drying time is 30-
Cooling time in 40min, the S7 is 30-50min.
(3) beneficial effect
The invention has the following advantages:
The method of the preparation acetylation hyaluronic acid prepares formamide solvent, Sodium Hyaluronate and the acetic anhydride of different volumes；
The formamide solvent of preparation is placed into a container, then the Sodium Hyaluronate of preparation is scattered containing formyl
In the container of amine solvent, dissolved；
Acetic anhydride is added in containing Sodium Hyaluronate and formamide solvent container again；
And then inside that Sodium Hyaluronate, formamide solvent and acetic anhydride in container is discharged into blender, passes through blender
Sodium Hyaluronate, formamide solvent and acetic anhydride are stirred and are reacted, new product is formed；
The Sodium Hyaluronate stirred inside blender, formamide solvent and acetic anhydride are stirred again and reacted to be formed newly
Product carries out precipitation process；
And then the product of precipitating is placed into the inside of washing facility, carried out by product of the washing facility to precipitating washed
Filter processing；
The product of carrying out washing treatment is finally placed into the inside of spray drying machine, spray drying is carried out by product of the spray drying machine to carrying out washing treatment
Processing is being cooled down after spray drying processing, is obtaining acetylation hyaluronic acid, and not only technique is simple and direct, convenient for making, and yield
Production cost greatly reduces in height, and small to molecule extent of the destruction, and original hyalomitome will be substantially improved after adding acetyl group
The water conservation moistening effect of sour sodium.
Certainly, it implements any of the products of the present invention and does not necessarily require achieving all the advantages described above at the same time.
Detailed description of the invention
Fig. 1 is preparation step schematic diagram of the present invention.
Specific embodiment
First embodiment
Following will be combined with the drawings in the embodiments of the present invention, and technical solution in the embodiment of the present invention carries out clearly and completely
Description, it is clear that described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.Based on this hair
Embodiment in bright, every other implementation obtained by those of ordinary skill in the art without making creative efforts
Example, shall fall within the protection scope of the present invention.
In the description of the present invention, it is to be understood that, term " aperture ", "upper", "lower", " thickness ", "top", " in ",
Indicating positions or the positional relationship such as " length ", "inner", " surrounding ", are merely for convenience of description of the present invention and simplification of the description, without
It is that the component of indication or suggestion meaning or element must have a particular orientation, is constructed and operated in a specific orientation, therefore not
It can be interpreted as limitation of the present invention.
Referring to Fig. 1, the embodiment of the present invention provides a kind of technical solution: a kind of method packet preparing acetylation hyaluronic acid
It includes, following steps:
S1, prepare material: preparing formamide solvent, Sodium Hyaluronate and the acetic anhydride of different volumes, Sodium Hyaluronate molecular weight
Range is without limitation；
S2, dissolution: the formamide solvent prepared in S1 is placed into a container, then the Sodium Hyaluronate prepared in S1 is divided
It dissipates and is placed into the container containing formamide solvent, dissolved；
S3, addition: the acetic anhydride in S1 is added in S2 containing in Sodium Hyaluronate and formamide solvent container；
S4, stirring: Sodium Hyaluronate, formamide solvent and the acetic anhydride in S3 container are discharged into the inside of blender again, passed through
Blender is stirred and reacts to Sodium Hyaluronate, formamide solvent and acetic anhydride, forms new product；
The Sodium Hyaluronate, formamide solvent and the acetic anhydride that stir inside blender in S4: being stirred by S5, precipitating again and instead
Formed new product is answered to carry out precipitation process；
The product precipitated in S5: being placed into the inside of washing facility by S6, washing again, the production by washing facility to precipitating in S5
Object carries out washing filtration treatment；
The product of carrying out washing treatment in S5: being finally placed into the inside of spray drying machine by S7, spray drying, by spray drying machine to washup in S5
The product of reason carries out spray drying processing and is being cooled down after spray drying processing, obtaining acetylation hyaluronic acid.
The ratio of formamide solvent and acetic anhydride mixed solvent in acetic anhydride final concentration 5%-10%, the S1 in the S1
For 2:4；And the ratio of hyaluronic acid and formamide solvent and acetic anhydride summation is 1.5:20-55.
Sodium Hyaluronate in the S1 is solid powdery, in order to preferably be dissolved in formamide solvent.
Formamide solvent in the S1 is organic formamide solvent.
In the S3 acetic anhydride addition is contained into Sodium Hyaluronate and formamide solvent container in S2, needed in acyclic acidic
It is operated simultaneously under border, carries out acetylization reaction, and acylation reaction temperature is 10-30 DEG C, when reaction solution is transparent.
The time 10-20min of the stirring of blender in the S4, in order to Sodium Hyaluronate, formamide solvent and acetic acid
Acid anhydride is adequately mixed, and the effect of subsequent reactions is improved, and improves the quality of acetylation hyaluronic acid.
Sedimentation time in the S5 is 30-45min, in order to which sediment preferably carries out separating with water source liquid point
Layer preferably carries out washing filtering in order to subsequent.
The temperature inside spray drying machine in the S7 is 200 DEG C -300 DEG C, and the spray drying time is 30-40min, the S7
In cooling time be 30-50min, herein temperature be 200 DEG C -300 DEG C, mainly can quickly to wash it is filtered
Product is dried, and improve dry efficiency, and spray drying parameter: air inlet flow is 300m3/h, and inlet air temperature is 200 °
C, leaving air temp are 80 °C, sprinkler pressure 0.125MPa, and spray speed is 500ml/h.
In use, preparing formamide solvent, Sodium Hyaluronate and the acetic anhydride of different volumes；
The formamide solvent of preparation is placed into a container, then the Sodium Hyaluronate of preparation is scattered containing formyl
In the container of amine solvent, dissolved；
Acetic anhydride is added in containing Sodium Hyaluronate and formamide solvent container again；
And then inside that Sodium Hyaluronate, formamide solvent and acetic anhydride in container is discharged into blender, passes through blender
Sodium Hyaluronate, formamide solvent and acetic anhydride are stirred and are reacted, new product is formed；
The Sodium Hyaluronate stirred inside blender, formamide solvent and acetic anhydride are stirred again and reacted to be formed newly
Product carries out precipitation process；
And then the product of precipitating is placed into the inside of washing facility, carried out by product of the washing facility to precipitating washed
Filter processing；
The product of carrying out washing treatment is finally placed into the inside of spray drying machine, spray drying is carried out by product of the spray drying machine to carrying out washing treatment
Processing is being cooled down after spray drying processing, is obtaining acetylation hyaluronic acid.
Second embodiment
A kind of method preparing acetylation hyaluronic acid further includes following steps:
S1, prepare material: preparing formamide solvent, Sodium Hyaluronate and acetic anhydride；
S2, dissolution: the formamide solvent prepared in S1 is placed into a container, then the Sodium Hyaluronate prepared in S1 is divided
It dissipates and is placed into the container containing formamide solvent, dissolved；
S3, addition: the acetic anhydride in S1 is added in S2 containing in Sodium Hyaluronate and formamide solvent container；
S4, stirring: Sodium Hyaluronate, formamide solvent and the acetic anhydride in S3 container are discharged into the inside of blender again, passed through
Blender is stirred and reacts to Sodium Hyaluronate, formamide solvent and acetic anhydride, forms new product；
The Sodium Hyaluronate, formamide solvent and the acetic anhydride that stir inside blender in S4: being stirred by S5, precipitating again and instead
Formed new product is answered to carry out precipitation process；
The product precipitated in S5: being placed into the inside of washing facility by S6, washing again, the production by washing facility to precipitating in S5
Object carries out washing filtration treatment；
The product of carrying out washing treatment in S5: being finally placed into the inside of spray drying machine by S7, spray drying, by spray drying machine to washup in S5
The product of reason carries out spray drying processing and is being cooled down after spray drying processing, obtaining acetylation hyaluronic acid.
The ratio of formamide solvent and acetic anhydride mixed solvent in acetic anhydride final concentration 7%-12%, the S1 in the S1
For 1.5:4；And the ratio of hyaluronic acid and formamide solvent and acetic anhydride summation is 1.2:20-35.
Sodium Hyaluronate in the S1 is solid powdery.
Formamide solvent in the S1 is organic formamide solvent.
In the S3 acetic anhydride addition is contained into Sodium Hyaluronate and formamide solvent container in S2, needed in acyclic acidic
It is operated simultaneously under border, carries out acetylization reaction, and acylation reaction temperature is 10-30 DEG C, when reaction solution is transparent.
The time 15-25min of the stirring of blender in the S4.
Sedimentation time in the S5 is 35-50min.
The temperature inside spray drying machine in the S7 is 230 DEG C -350 DEG C, and the spray drying time is 25-35min, the S7
In cooling time be 30-40min, and spray drying parameter: air inlet flow is 300m3/h, and inlet air temperature is 200 °C, out wind-warm syndrome
Degree is 150 °C, sprinkler pressure 0.135MPa, and spray speed is 550ml/h.
3rd embodiment
A kind of method preparing acetylation hyaluronic acid further includes following steps:
S1, prepare material: preparing formamide solvent, Sodium Hyaluronate and acetic anhydride；
S2, dissolution: the formamide solvent prepared in S1 is placed into a container, then the Sodium Hyaluronate prepared in S1 is divided
It dissipates and is placed into the container containing formamide solvent, dissolved；
S3, addition: the acetic anhydride in S1 is added in S2 containing in Sodium Hyaluronate and formamide solvent container；
S4, stirring: Sodium Hyaluronate, formamide solvent and the acetic anhydride in S3 container are discharged into the inside of blender again, passed through
Blender is stirred and reacts to Sodium Hyaluronate, formamide solvent and acetic anhydride, forms new product；
The Sodium Hyaluronate, formamide solvent and the acetic anhydride that stir inside blender in S4: being stirred by S5, precipitating again and instead
Formed new product is answered to carry out precipitation process；
The product precipitated in S5: being placed into the inside of washing facility by S6, washing again, the production by washing facility to precipitating in S5
Object carries out washing filtration treatment；
The product of carrying out washing treatment in S5: being finally placed into the inside of spray drying machine by S7, spray drying, by spray drying machine to washup in S5
The product of reason carries out spray drying processing and is being cooled down after spray drying processing, obtaining acetylation hyaluronic acid.
The ratio of formamide solvent and acetic anhydride mixed solvent in acetic anhydride final concentration 5%-10%, the S1 in the S1
For 2.3:5；And the ratio of hyaluronic acid and formamide solvent and acetic anhydride summation is 2:25-60.
Sodium Hyaluronate in the S1 is solid powdery.
Formamide solvent in the S1 is organic formamide solvent.
In the S3 acetic anhydride addition is contained into Sodium Hyaluronate and formamide solvent container in S2, needed in acyclic acidic
It is operated simultaneously under border, carries out acetylization reaction, and acylation reaction temperature is 15-35 DEG C, when reaction solution is transparent.
The time 15-20min of the stirring of blender in the S4.
Sedimentation time in the S5 is 20-30min.
The temperature inside spray drying machine in the S7 is 150 DEG C -200 DEG C, and the spray drying time is 35-43min, the S7
In cooling time be 20-30min and spray drying parameter: air inlet flow is 380m3/h, and inlet air temperature is 150 °C, leaving air temp
It is 100 °C, sprinkler pressure 0.155MPa, spray speed is 500ml/h.
It should be noted that, in this document, relational terms such as first and second and the like are used merely to a reality
Body or operation are distinguished with another entity or operation, are deposited without necessarily requiring or implying between these entities or operation
In any actual relationship or order or sequence.Moreover, the terms "include", "comprise" or its any other variant are intended to
Non-exclusive inclusion, so that the process, method, article or equipment including a series of elements is not only wanted including those
Element, but also including other elements that are not explicitly listed, or further include for this process, method, article or equipment
Intrinsic element.
Present invention disclosed above preferred embodiment is only intended to help to illustrate the present invention.There is no detailed for preferred embodiment
All details are described, are not limited the invention to the specific embodiments described.Obviously, according to the content of this specification,
It can make many modifications and variations.These embodiments are chosen and specifically described to this specification, is in order to better explain the present invention
Principle and practical application, so that skilled artisan be enable to better understand and utilize the present invention.The present invention is only
It is limited by claims and its full scope and equivalent.
Claims (8)
1. a kind of method for preparing acetylation hyaluronic acid, which is characterized in that including following steps:
S1, prepare material: preparing formamide solvent, Sodium Hyaluronate and the acetic anhydride of different volumes；
S2, dissolution: the formamide solvent prepared in S1 is placed into a container, then the Sodium Hyaluronate prepared in S1 is divided
It dissipates and is placed into the container containing formamide solvent, dissolved；
S3, addition: the acetic anhydride in S1 is added in S2 containing in Sodium Hyaluronate and formamide solvent container；
S4, stirring: Sodium Hyaluronate, formamide solvent and the acetic anhydride in S3 container are discharged into the inside of blender again, passed through
Blender is stirred and reacts to Sodium Hyaluronate, formamide solvent and acetic anhydride, forms new product；
The Sodium Hyaluronate, formamide solvent and the acetic anhydride that stir inside blender in S4: being stirred by S5, precipitating again and instead
Formed new product is answered to carry out precipitation process；
The product precipitated in S5: being placed into the inside of washing facility by S6, washing again, the production by washing facility to precipitating in S5
Object carries out washing filtration treatment；
The product of carrying out washing treatment in S5: being finally placed into the inside of spray drying machine by S7, spray drying, by spray drying machine to washup in S5
The product of reason carries out spray drying processing and is being cooled down after spray drying processing, obtaining acetylation hyaluronic acid.
2. a kind of method for preparing acetylation hyaluronic acid according to claim 1, it is characterised in that: the second in the S1
Formamide solvent and the ratio of acetic anhydride mixed solvent are 2:4 in acid anhydrides final concentration 5%-10%, the S1；And hyaluronic acid with
The ratio of formamide solvent and acetic anhydride summation is 1.5:20-55.
3. a kind of method for preparing acetylation hyaluronic acid according to claim 1, it is characterised in that: saturating in the S1
Bright matter acid sodium is solid powdery.
4. a kind of method for preparing acetylation hyaluronic acid according to claim 1, it is characterised in that: the first in the S1
Amide solvent is organic formamide solvent.
5. a kind of method for preparing acetylation hyaluronic acid according to claim 1, it is characterised in that: by second in the S3
Acid anhydrides addition, containing Sodium Hyaluronate and formamide solvent container, is needed under acidic environment while being operated in S2, carries out second
Acylation reaction, and acylation reaction temperature is 10-30 DEG C, when reaction solution is transparent.
6. a kind of method for preparing acetylation hyaluronic acid according to claim 1, it is characterised in that: stirred in the S4
The time 10-20min of the stirring of machine.
7. a kind of method for preparing acetylation hyaluronic acid according to claim 1, it is characterised in that: heavy in the S5
The shallow lake time is 30-45min.
8. a kind of method for preparing acetylation hyaluronic acid according to claim 1, it is characterised in that: the spray in the S7
Temperature inside dry machine is 200 DEG C -300 DEG C, and the spray drying time is 30-40min, and the cooling time in the S7 is 30-
50min。
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| CN113045686A (en) * | 2021-03-03 | 2021-06-29 | 杭州华玮生物科技有限公司 | Preparation method of acetylated hyaluronic acid |
| CN113061198A (en) * | 2021-03-23 | 2021-07-02 | 段元俊 | Acetylated hyaluronic acid ester and preparation method thereof |
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| WO2022222607A1 (en) * | 2021-04-21 | 2022-10-27 | 山东焦点福瑞达生物股份有限公司 | Preparation method for acetylated sodium hyaluronate |
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| CN117586434A (en) * | 2023-11-14 | 2024-02-23 | 山东天晟生物科技有限公司 | Preparation method and application of acetylated sodium hyaluronate |
| CN117586434B (en) * | 2023-11-14 | 2024-08-09 | 山东天晟生物科技有限公司 | Preparation method and application of acetylated sodium hyaluronate |
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