CN104098620B - Beta-arbutin crystal V-shaped substance, preparation method, composition and application thereof - Google Patents
Beta-arbutin crystal V-shaped substance, preparation method, composition and application thereof Download PDFInfo
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Abstract
The invention discloses a beta-Arbutin crystal V type (chemical name: 4-hydroxyphenyl-beta-D-glucopyranoside, english name: arbutin), a preparation method thereof, a composition thereof and application thereof. Specifically, the invention discloses that beta-arbutin compound exists in a crystal V-shaped solid matter state form in a solid state; a preparation method of a crystal V-shaped solid substance sample; the application of beta-arbutin crystal V-shaped substance as an active ingredient in the preparation of antibacterial and anti-inflammatory medicaments and cosmetics.
Description
Technical Field
The invention relates to a crystal V-shaped solid substance state form of beta-arbutin existing in a solid state is discovered; relates to a preparation method of a crystal V-shaped sample; relates to a pharmaceutical composition or a cosmetic containing beta-arbutin crystal form V and a mixed crystal form containing crystal form V in any proportion; the invention also relates to application of the beta-arbutin crystal form substance as an active ingredient of a medicament or a cosmetic in preparing antibacterial and anti-inflammatory medicaments and cosmetics.
Background
The molecular structural formula of the beta-Arbutin crystal V (chemical name: 4-hydroxyphenyl-beta-D-pyran glucoside, english name: arbutin) is as follows:
chinese patent CN1302599A (publication number) describes "cosmetic composition containing N-ethoxycarbonyl-4-amino-phenol and arbutin or its derivative and/or ellagic acid or its derivative" of the invention of III, skoeli D, M, fam " [1] In particular to a preparation method of an arbutin cosmetic composition.
Chinese patent CN1481233A (publication number) describes "skin whitening composition containing arbutin and glucosidase as active ingredients" invented by Gaotai Limited " [2] Wherein, it relates to a skin whitening composition containing arbutin.
Chinese patent CN1228300A (publication number) describes "a preparation method of spot-removing and whitening gel cosmetic" in the invention of Luo xiu ying and Liangyuzhen " [3] In particular to a preparation method of a spot-removing and whitening gel cosmetic containing arbutin.
Chinese patent CN1208608A (publication number) describes the use of arbutin monoesters as depigmenting agents in the invention of M.Philippine " [4] Wherein use of arbutin monoesters as depigmenting or bleaching agents for human skin or the like in topically applied compositions is contemplated.
Chinese patent CN1608693A (publication number) describes that "a kind of arbutin-containing ginseng and American ginseng and their preparation method" [5] In particular to ginseng and American ginseng containing arbutin and a preparation method thereof.
Chinese patent CN1633980A (publication number) describes "a cosmetic prepared from arbutin-containing Ginseng radix" [6] In particular to a beauty cosmetic prepared by arbutin-containing ginseng.
Chinese patent CN1635139A (publication number) describes "method for producing alpha-arbutin by fermentation" invented by Liuchun skillful " [7] In particular to a preparation method of alpha-arbutin.
Chinese patent CN1724551A (publication number) describes a method for preparing alpha-arbutinPreparation method " [8] The method comprises the following steps of: ethyl acetate =9 to 7:1.
chinese patent CN1727493A (publication number) describes the invention of Zhangpeng, zhang Shurong, liuchuqiao and the like, namely the method for catalytically synthesizing alpha-arbutin by free cells or immobilized cells " [9] The method comprises the steps of preparing alpha-arbutin by using Xanthomonas campestris CGMCC NO.1243 free cells or immobilized cells as a catalyst, and using water as a recrystallization solvent in the last step.
Chinese patent CN101247816A (publication number) describes that "molecular complex containing arbutin, ascorbic acid, oleuropein and derivatives thereof" of the invention of M.Tutinono and related applications thereof in the field of medicine " [10] Wherein, it relates to a molecular complex containing fructoside, ascorbic acid, oleuropein or its derivatives, and the related application in the medical field.
An arbutin multifunctional skin care lotion is recorded in Chinese patent CN101732169A (publication number) " [11] In particular to a multifunctional skin care lotion containing arbutin.
Chinese patent CN101597631A (publication number) describes "a method for producing A-arbutin by fermentation and transformation of Rhizopus, ponzonwen and von 26052525252525; [12] in particular to a method for producing A-arbutin by fermenting and converting rhizopus.
Chinese patent CN102040636A (publication number) describes the synthesis of beta-arbutin from alpha-D-glucose pentaacetate of Lianliang, yang Shuqin and Guo Xiu Ru " [13] The method comprises the steps of taking alpha-D-glucose pentaacetate as a raw material to synthesize a key intermediate so as to synthesize beta-arbutin, and adopting ethanol and water as a recrystallization solvent in the last step.
Chinese patent CN102093442A (publication number) describes a method for separating and purifying arbutin from blueberry, which is invented by Zhao Yuhong, wang Zhen Yu and Wang jin Ling " [14] Wherein the arbutin extracted from blueberry pomace is separated and purifiedThe method of (1), wherein the solvent for the final recrystallization step is water.
Chinese patent CN102505031A (publication number) describes "method for synthesizing arbutin by converting hydroquinone into baicalin using hairy roots of Scutellariae radix" invented by Qixiangjun, pengfuyu, qianyongdong and Shichunyang " [15] In particular to a method for synthesizing arbutin by converting hydroquinone through hairy roots of scutellaria baicalensis.
Chinese patent CN102329838A (publication number) describes the invention of Dugang and Yanhaiying, a process for producing alpha-arbutin by microbial transformation " [16] In particular to a method for producing alpha-arbutin by transforming aspergillus niger strains.
Chinese patent CN102517361A (publication number) describes a method for synthesizing arbutin by lipase catalysis, which is invented by Dengli, liuchun Qiao, wang Fang, tan Tianwei, nie Kai and Cao Xi " [17] In particular to a preparation method for synthesizing arbutin by using free or immobilized porcine pancreatic lipase.
Chinese patent CN102517362A (publication number) describes a method for catalytic synthesis of alpha-arbutin by lipase, which is invented by Wang Fang, liuchun Qiao, dengli, tan Tianwei, nie Kali and Cao Xi " [18] The method comprises a step of preparing alpha-arbutin by using free or immobilized candida lipase for catalytic synthesis, wherein water is used as a recrystallization solvent in the last step.
Chinese patent CN102697672A (publication number) describes Arbutin multiple emulsion of Xiagong and Chenyangling invention and its preparation method " [19] Wherein, the arbutin multiple emulsion is provided, and the carrier is loaded with arbutin active ingredients.
The article "Arbutin: isolation, X-ray Structure and functional students" by Jacek E.Nycz et al is described in the Journal of Molecular Structure, abroad " [20] Wherein a beta-arbutin crystal form containing 0.5 water molecules is involved.
The invention discovers a beta-arbutin crystal form V solid substance state without crystal water and a preparation method thereof, which are different from the contents of the patent or the literature research report.
The research aim of the invention is to start from the research of the existence state of the crystal form solid matter of beta-arbutin, search and discover the existence type and state characteristics of the crystal form solid matter on the level of the raw materials of the active ingredients of the drugs and cosmetics through a crystal form screening technology and a crystal form bioactivity evaluation technology, combine the crystal form matter with the biological effectiveness research, and provide basic scientific data for searching, discovering and developing the superior medicinal crystal form solid matter of the beta-arbutin with the optimal clinical curative effect; meanwhile, a scientific basis is provided for applying for national or international intellectual property patent protection on the basis of the beta-arbutin solid drug raw material.
Disclosure of Invention
One of the objects of the present invention is: the existence state and description mode of the beta-arbutin crystal form V solid matter are provided.
The second object of the present invention is: provides a preparation method of a beta-arbutin crystal V-shaped solid substance sample.
The third object of the present invention is: provides a solid medicine containing beta-arbutin crystal form V pure product or mixed crystal form containing crystal form V in any proportion and a composition thereof.
The fourth object of the present invention is: providing a pharmaceutical composition using beta-arbutin crystal form V solid matter as a pharmaceutically active ingredient, wherein the daily dosage of the pharmaceutical composition is within the range of 10-500 mg; provides a cosmetic using beta-arbutin crystal form solid matter as an effective ingredient, and the daily dosage of the cosmetic is within the range of 100-1000 mg.
The fifth purpose of the invention is: provides a tablet, a capsule, a pill, an injection, a sustained-release or controlled-release preparation medicament for clinical use prepared and developed by using the crystal V-shaped solid substance of beta-arbutin as a raw material of a medicinal active ingredient; cosmetics in the form of solid, suspension, emulsion or paste using the crystalline solid substance of beta-arbutin as an active ingredient are provided.
The sixth purpose of the invention is: provides beta-arbutin crystal V-shaped substance which can improve the blood concentration in organisms due to the crystal substance in the process of treating diseases so as to play the effective treatment role of the medicine.
The seventh of the purposes of the present invention: provides the application of the crystal V-shaped solid substance of beta-arbutin as an active ingredient raw material in preparing antibacterial and anti-inflammatory medicaments and cosmetics.
The invention provides a crystal V-shaped solid substance form of a beta-arbutin compound in a solid state and a preparation method of a crystal V-shaped sample; the application of the medicaments and the compositions thereof prepared and developed by using different crystal substances of beta-arbutin as active ingredients in the preparation of antibacterial and anti-inflammatory medicaments and cosmetics is found.
Characteristic of the technology
1. The crystal V-shaped solid sample morphological characteristics of the beta-arbutin are as follows:
1.1 the present invention relates to a beta-arbutin crystal form V solid substance characterized by using CuK when powder X-ray diffraction analysis is used a The diffraction peak position is 2-Theta value (degree) or d value under the irradiation experiment condition
Solid matter when the diffraction peak relative intensity peak Height value (Height%) or peak Area value (Area%) has the following characteristic peaks (table 1, fig. 1):
TABLE 1 powder X-ray diffraction Peak of beta-arbutin Crystal form V solid sample
1.2 the beta-arbutin crystal form V solid substance of the present invention is characterized by showing a crystal form V of 3313, 2973, 2892, 2127, 2028, 2000, 1865, 1644, 1603, 1508, 1371, 1210, 1094, 1067, 1036, 1009, 893, 828, 776, 658cm when analyzed by infrared spectroscopy -1 Has characteristic peaks of infrared spectrum, wherein the allowable deviation of the characteristic peaks of the infrared spectrum is +/-2 cm -1 (FIG. 2).
1.3 the beta-arbutin crystal form V solid matter of the present invention is characterized by showing 1 exothermic peak at 85 ℃ plus or minus 3 ℃ and 1 endothermic peak at 198 ℃ plus or minus 3 ℃ in DSC chart with a temperature rise rate of 10 ℃ per minute using differential scanning calorimetry (FIG. 3).
2. The preparation method of the beta-arbutin crystal V-shaped sample is characterized by comprising the following steps:
the invention relates to a preparation method of a beta-arbutin crystal V-shaped sample, which is characterized by placing the sample in a thermostat with the temperature of more than or equal to 200 ℃ for 10-30 min to completely melt the sample, and placing the sample in the thermostat with the environmental temperature of 20-60 ℃ after melting to obtain an arbutin crystal V-shaped solid substance.
3. The crystal form components, administration dosage and pharmaceutical preparation composition of the beta-arbutin are characterized in that:
3.1 the beta-arbutin mixed crystal solid matter is characterized by containing beta-arbutin crystal V-shaped components in any proportion.
3.2 the pharmaceutical composition or the cosmetic is characterized by containing beta-arbutin crystal V type or beta-arbutin mixed crystal solid matter and a pharmaceutically acceptable carrier.
3.3 the dosage of the beta-arbutin for the pharmaceutical composition is within the range of 10-500 mg per day.
3.4 in the cosmetic, the daily dosage of the beta-arbutin is within the range of 100-1000 mg.
3.5 the invention relates to a pharmaceutical composition, which is characterized in that the pharmaceutical composition is various tablets, capsules, pills, injections, sustained release preparations and controlled release preparations.
The invention relates to a cosmetic, which is characterized by being solid, suspension, emulsion or paste.
3.7 the invention relates to the application of beta-arbutin crystal V or the mixed crystal component containing beta-arbutin crystal V in any proportion in the preparation of antibacterial and anti-inflammatory drugs and cosmetics.
Drawings
FIG. 1 powder X-ray diffraction pattern of beta-arbutin crystal V-shaped solid sample
FIG. 2 is an infrared absorption spectrum of a beta-arbutin crystal form V sample
FIG. 3 differential scanning calorimetry of beta-arbutin crystal form V sample
Detailed Description
The following examples are given for better illustration of the technical solution of the present invention, but the present invention is not limited thereto.
Example 1
Preparation method of beta-arbutin crystal V-shaped sample 1:
placing 200mg of beta-arbutin bulk drug in a thermostat at 200 ℃ for 10min to completely melt the sample, placing the melted sample at 60 ℃ in the environment, and performing powder X-ray diffraction analysis on the obtained sample, wherein the diffraction pattern of the sample is consistent with that of figure 1, and the obtained sample is a beta-arbutin crystal V-shaped solid substance.
placing 200mg of beta-arbutin bulk drug in a thermostat at 200 ℃ for 30min to completely melt the sample, placing the sample at the ambient temperature of 30 ℃ after melting, and performing powder X-ray diffraction analysis on the obtained sample, wherein the diffraction pattern of the sample is consistent with that of figure 1, and the obtained sample is a beta-arbutin crystal V-shaped solid substance.
Example 2
Method for the preparation of a combined pharmaceutical preparation 1 (tablet):
a preparation method of a combined medicine tablet is characterized in that a pure beta-arbutin crystal V-shaped product or a mixed crystal solid matter containing crystal V-shaped in any proportion is used as a raw material medicine of the combined medicine, a plurality of excipients are used as auxiliary material components for preparing the combined medicine tablet, a tablet sample with the medicine content of 10-300 mg is prepared according to a certain proportion, and the formula proportion of the tablet is given in a table 2:
TABLE 2 preparation formulation of beta-arbutin pharmaceutical tablets
The method for preparing the pure beta-arbutin crystal V-shaped product or the mixed crystal bulk drug containing crystal V-shaped in any proportion into the tablet preparation comprises the following steps: mixing several excipients with the raw materials, adding appropriate amount of 1% sodium carboxymethylcellulose solution, making into soft material, sieving, granulating, oven drying, sieving, grading, adding magnesium stearate and pulvis Talci, mixing, and tabletting.
a preparation method of a combined medicine capsule is characterized in that a pure beta-arbutin crystal V-shaped product or a mixed crystal solid matter containing crystal V-shaped in any proportion is used as a raw material medicine of the combined medicine, a plurality of excipients are used as auxiliary material components for preparing the combined medicine capsule, a capsule sample with the medicine content of 10-200 mg is prepared according to a certain proportion, and the formula proportion of the capsule is given in a table 3:
TABLE 3 bulk drug and adjuvant formulation for beta-arbutin crystal V-shaped combined drug capsule preparation
The method for preparing the beta-arbutin crystal V-shaped pure product or the mixed crystal bulk drug containing crystal V-shaped in any proportion into the tablet preparation comprises the following steps: mixing several excipients with the raw materials, adding appropriate amount of 1% sodium carboxymethylcellulose solution, making into wet granules, oven drying, sieving, grading, adding magnesium stearate, mixing, and making into capsule; or directly mixing beta-arbutin bulk drug and a plurality of excipient auxiliary materials without using a granulation step, sieving and directly encapsulating to obtain the product.
Preparation method of cosmetic 3 (powder):
a preparation method of cosmetics is characterized in that a pure beta-arbutin crystal V-shaped product or a mixed crystal solid substance containing crystal V-shaped crystals in any proportion is used as a raw material medicine of the cosmetics, a plurality of excipients are used as auxiliary material components for preparing the cosmetics, powder with the content of 100-500 mg is prepared according to a certain proportion, and the formula proportion of the cosmetic powder is given in a table 4:
TABLE 4 formula of beta-arbutin crystal V-shaped cosmetic powder
The ingredients of the formula are crushed and sieved by a 200-mesh sieve, and the ingredients are uniformly mixed, tabletted and boxed to prepare the pressed powder.
Preparation method of cosmetic 4 (suspension):
a preparation method of cosmetics is characterized in that pure beta-arbutin crystal V-shaped products or mixed crystal solid substances containing crystal V-shaped in any proportion are used as raw materials of the cosmetics, a plurality of excipients are used as auxiliary materials for preparing the cosmetics, suspension with the content of 100-500 mg is prepared according to a certain proportion, and the formula proportion of the cosmetic suspension is given in a table 5:
TABLE 5 beta-arbutin crystal form V cosmetic suspension formulation
Pulverizing the above materials, sieving with 200 mesh sieve, adding glycerol and water, ultrasonic processing to obtain suspension, and bottling.
Preparation method of cosmetic 5 (emulsion or cream):
a preparation method of cosmetics is characterized in that a beta-arbutin crystal V-shaped pure product or a mixed crystal solid substance containing crystal V in any proportion is used as a raw material medicine of the cosmetics, a plurality of excipients are used as auxiliary material components for preparing the cosmetics, and emulsion or ointment with the content of 100-500 mg is prepared according to a certain proportion, and the formula proportion of the cosmetic emulsion or ointment is given in Table 6:
TABLE 6 cosmetic emulsion or paste formulation of beta-arbutin crystal form V
Pulverizing the above components, sieving with 200 mesh sieve, adding appropriate amount of glycerol and a little water, stirring, mixing the samples, and bottling.
Example 3
Administration dose 1 (tablet) of the beta-arbutin crystal form combination medicament:
the pharmaceutical composition developed is prepared by using a crystal form beta-arbutin sample as a pharmaceutical active ingredient, and is characterized in that crystal form V beta-arbutin is used as the pharmaceutical active ingredient, the daily administration dose is 30mg, and the pharmaceutical composition can be respectively prepared into 1 10mg common tablets 3 times a day per time, 1 15mg common tablets 2 times a day per time or 130 mg common tablets 1 time a day per time.
Administration dose 2 (capsule) of the beta-arbutin crystal form combined drug:
the pharmaceutical composition prepared and developed by using the crystal form beta-arbutin sample as the active pharmaceutical ingredient is characterized in that the crystal form V-arbutin is used as the active pharmaceutical ingredient, the daily administration dosage is 60mg, and the pharmaceutical composition can be respectively prepared into 1 capsule with 30mg for 1 capsule 1 time/1 day.
Problems to be explained: the beta-arbutin crystal form pharmaceutical composition has many factors on the administration dosage of the effective ingredients, such as: the use for prevention and treatment varies with the daily dosage; the nature and severity of the disease cause different daily doses; the daily dosage of the medicament is different due to different sexes, ages and body surface areas of patients, different administration routes, administration times and treatment purposes; in addition, the difference of absorption and blood concentration existing among crystal form samples also causes that the daily proper dosage range of the beta-arbutin crystal form component used in the invention is 0.01-300mg/kg of body weight, preferably 10-100mg/kg of body weight. When in use, different total dosage schemes of the V-shaped crystal beta-arbutin active ingredients are formulated according to different requirements of actual prevention and treatment of different conditions, and the administration can be completed in a multi-time or one-time mode.
The dosage of the beta-arbutin crystal form cosmetic is as follows:
the crystal form beta-arbutin sample is used as an active ingredient to prepare and develop the cosmetic night cream, and the crystal form V-type beta-arbutin is used as the active ingredient of the cosmetic, the daily dosage is 200mg, and the cosmetic night cream is used at night.
The developed cosmetic foundation cream is prepared by using a crystal form beta-arbutin sample as an active ingredient, and is characterized in that crystal form V beta-arbutin is used as the active ingredient of the cosmetic, the daily dosage is 100mg, and the cosmetic foundation cream is used in the morning.
Example 4
The beta-arbutin crystal V-shaped absorption advantage:
the beta-arbutin crystal V-shaped solid substance belongs to an absorption advantage crystal form, and has higher absorption advantage characteristics than other crystal forms when being taken orally or externally used.
Reference to the literature
1. Chinese patent, publication No. CN1302599A
2. Chinese patent, publication No. CN1481233A
3. Chinese patent, publication No. CN1228300A
4. Chinese patent, publication No. CN1208608A
5. Chinese patent, publication No. CN1608693A
6. Chinese patent, publication No. CN1633980A
7. Chinese patent, publication No. CN1635139A
8. Chinese patent, publication No. CN1724551A
9. Chinese patent, publication No. CN1727493A
10. Chinese patent, publication No. CN101247816A
11. Chinese patent, publication No. CN101732169A
12. Chinese patent, publication No. CN101597631A
13. Chinese patent, publication No. CN102040636A
14. Chinese patent, publication No. CN102093442A
15. Chinese patent, publication No. CN102505031A
16. Chinese patent, publication No. CN102329838A
17. Chinese patent, publication No. CN102517361A
18. Chinese patent, publication No. CN102517362A
19. Chinese patent, publication No. CN102697672A
20.Jacek E.Nycz,Grzegorz Malecki,Monika Morag,et al.Arbutin:Isolation,X-ray structure and computional studies.Journal of Molecular Structure.2010,980:13-17.
Claims (10)
1. Beta-arbutin crystal form V solid substance characterized by using CuK when analyzed using powder X-ray diffraction a Diffraction peak position 2-Theta value (degree) or d value under irradiation experiment condition
The diffraction peak relative intensity peak Height (Height%) or peak Area value (Area%) is represented as follows:
when analyzed using infrared spectroscopy at 3313, 2973, 2892, 2127, 2028, 2000, 1865, 1644, 1603, 1508, 1371, 1210, 1094, 1067, 1036, 1009, 893, 828, 776, 658cm -1 Has characteristic peaks of infrared spectrum, wherein the allowable deviation of the characteristic peaks of the infrared spectrum is +/-2 cm -1 (ii) a When analyzed using differential scanning calorimetry, it was shown that there were 1 exothermic peak at a temperature of 85 ℃. + -. 3 ℃ and 1 endothermic peak at a temperature of 198 ℃. + -. 3 ℃ in a DSC chart with a temperature rise rate of 10 ℃ per minute.
2. The method for preparing a crystalline V-shaped solid substance of beta-arbutin according to claim 1, wherein the crystalline V-shaped solid substance of beta-arbutin is obtained by placing the crystalline V-shaped solid substance of beta-arbutin in a thermostat with a temperature of 200 ℃ or higher for 10min to 30min to completely melt the sample, and placing the sample in an environment with an ambient temperature of 20 ℃ to 60 ℃ after melting.
3. A mixed crystal form solid matter of beta-arbutin, which is characterized by containing the beta-arbutin crystal form V component in any proportion in claim 1.
4. A pharmaceutical composition or cosmetic comprising the purified form V of β -arbutin crystal according to claim 1 and a pharmaceutically acceptable carrier.
5. A pharmaceutical composition or cosmetic comprising the solid substance of mixed crystal form of β -arbutin according to claim 3 and a pharmaceutically acceptable carrier.
6. Pharmaceutical composition according to claim 4 or 5, characterized in that the daily dose of β -arbutin is in the range of 10 to 500 mg.
7. The cosmetic according to claim 4 or 5, wherein the daily dose of β -arbutin is in the range of 100 to 1000 mg.
8. The pharmaceutical composition according to claim 4 or 5, wherein the dosage form of the composition is a tablet, a capsule, a pill, an injection, a sustained release formulation or a controlled release formulation.
9. The cosmetic according to claim 4 or 5, wherein said cosmetic is in the form of a solid, suspension, emulsion or cream.
10. Use of the beta-arbutin crystal form V of claim 1 and/or the mixed crystal form solid substance of claim 3 in the preparation of antibacterial and anti-inflammatory drugs and cosmetics.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1043321A1 (en) * | 1999-03-29 | 2000-10-11 | Nisshin Flour Milling Co., Ltd. | Process for the preparation of tetrahydropyran derivatives |
| CN101938974A (en) * | 2007-11-14 | 2011-01-05 | Omp有限公司 | Skin treatment compositions |
-
2013
- 2013-04-09 CN CN201310120489.1A patent/CN104098620B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1043321A1 (en) * | 1999-03-29 | 2000-10-11 | Nisshin Flour Milling Co., Ltd. | Process for the preparation of tetrahydropyran derivatives |
| CN101938974A (en) * | 2007-11-14 | 2011-01-05 | Omp有限公司 | Skin treatment compositions |
Non-Patent Citations (3)
| Title |
|---|
| Arbutin: Isolation, X-ray structure and computional studies;Jacek E. Nycz，等;《Journal of Molecular Structure》;20100910;第980卷(第1-3期);第13–17页 * |
| 卡斯坦森.无定形.《现代药用粉体微粒学》.中国医药科技出版社,2004,(第1版),第78页. * |
| 熊果苷的合成;周烽，等;《香料香精化妆品》;20050831(第4期);第11-12页 * |
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