CN108285407A - The extracting method of hydroxytyrosol in olive oil processing waste - Google Patents
The extracting method of hydroxytyrosol in olive oil processing waste Download PDFInfo
- Publication number
- CN108285407A CN108285407A CN201810032952.XA CN201810032952A CN108285407A CN 108285407 A CN108285407 A CN 108285407A CN 201810032952 A CN201810032952 A CN 201810032952A CN 108285407 A CN108285407 A CN 108285407A
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- China
- Prior art keywords
- olive
- hydroxytyrosol
- cake
- ethyl acetate
- extracting method
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/005—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from products, waste products or side-products of processes, not directed to the production of phenols, by conversion or working-up
- C07C37/009—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from products, waste products or side-products of processes, not directed to the production of phenols, by conversion or working-up from waste water
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Environmental & Geological Engineering (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a kind of extracting methods of hydroxytyrosol in olive oil processing waste, include the following steps：（1）The olive cake that gives up is freeze-dried；（2）It takes dried olive to give up cake, n-hexane extraction, removal fat is added；（3）Take step（2）Obtained degreasing product is added NaOH and is hydrolyzed, hydrolysate is then acidified to pH3 4 with HCl；（4）The BPC discharged in clear solution is extracted with ethyl acetate, mixed acetic acid ethyl acetate extract is evaporated in vacuo, residue is hydroxytyrosol extract.The present invention carries out the preparation of hydroxytyrosol using olive waste, and obtaining hydroxytyrosol has the function of anti-oxidant etc., can be adapted for skin resisting oxidation and delaying senility purposes.
Description
Technical field
The invention belongs to compound extractive technique fields, and in particular to hydroxytyrosol in a kind of olive oil processing waste
Extracting method.
Background technology
The aging of skin and the aging of body are carried out at the same time, and skin aging is a part for body aging.Skin position
In the outermost layer of body, it is more affected by the influence of extrinsic factor, therefore the aging of skin is endogenous factor and exogenous
The coefficient result of factor.The exogenous aging of skin and ultraviolet light（UV）Irradiation, wind, contact with stimulant it is related.
And the long-term irradiation of UV is to promote the main factor of skin aging in environment, in the investigation of wrinkle of skin and dietary structure relationship
Crowd's wrinkle of skin of middle discovery, daily large amounts of food olive products is relatively fewer.Research finds that the free radical of olive polyphenol is clear
Removing solid capacity, which generates skin health, directly to be influenced, including prevents oxidation related with wrinkle formation, thinning of skin and water shortage
Effect.By simulating intravital situation, cause superoxide anion in tissue and intracellular life after being irradiated by ultraviolet light such as skin
At polyphenol has Scavenging activity to active oxygen such as superoxide anion in display olive berry extract.The single electron of oxygen in organism
Reduction, the enzymatic oxidation and autoxidation of biomolecule can all generate various oxygen radicals.The strong reactivity of these free radicals is to lead
The main reason for causing cell oxidative damage and aging.By showing olive to polyphenols Study on Its Antioxidant Activity in Vitro in olive
There is olive polyphenols good antioxygenic property to show apparent advantage especially in terms of scavenging hydroxyl,
Damages of Epidermal Permeability Barrier can be repaired, light aging wrinkle caused by forming ultraviolet light is prevented.
Canarium Oleaceae, Olea aiphyllium, are world-renowned woody oil tree species, there is cultivation in more than 4000 years
Train history.Olive is mainly distributed on mediterranean country, and Greece, Italy, Tunisia, Spain are intensively.With olive
The olive oil that fruit squeezes has more rich in a variety of active ingredients such as unsaturated fatty acid, aldehydes matter and liposoluble vitamins
Kind health-care efficacy, is ideal table oil.Currently, in olive oil process, olive fresh fruit is through defibrination, centrifugation point
After producing virgin oil, a large amount of pomace and waste liquid are generated, contains the various actives such as Marc oil, polyphenol and terpenoid
The olive oil processing waste (Olive oil processing waste, OPW) of ingredient does not obtain effective high-valued profit
With causing the great wasting of resources and environmental pollution.It is urgently to solve that OPW how has been developed and used while producing olive oil
Certainly the technical issues of.The main component of olive pomace is lignin, cellulose, Marc oil, aldehydes matter and triterpene compound
Deng wherein aldehydes matter is ingredient mostly important in olive, wherein main aldehydes matter has hydroxytyrosol, olive bitter
Glycosides, caffeic acid, ferulic acid, gallic acid etc..Hydroxytyrosol is the ingredient of most antioxidant activity effect, is also always the country
The hot spot of outer research.In the process of olive oil, the aldehydes matter for being dissolved in olive oil has anti-oxidant, anti-inflammatory, antibacterial etc.
The olive polyphenol substance of multi-efficiency is lost in the discarded of OPW.The aldehydes matter extracted from OPW, can be used as food and
Good antioxidant in medical industry, exploitation olive polyphenol, especially hydroxytyrosol product for olive oil processing enterprise and
The profit of waste is used to say that a very potential development field.
Invention content
The purpose of the present invention is to provide a kind of extracting methods of hydroxytyrosol in olive oil processing waste.
The technical solution used in the present invention is：
The extracting method of hydroxytyrosol, includes the following steps in a kind of olive oil processing waste：
（1）The olive cake that gives up is freeze-dried；
（2）It takes dried olive to give up cake, n-hexane extraction, removal fat is added；
（3）Take step（2）Obtained degreasing product is added NaOH and is hydrolyzed, hydrolysate is then acidified to pH3- with HCl
4, obtain clear solution；
（4）Clear solution is extracted with ethyl acetate, mixed acetic acid ethyl acetate extract is evaporated in vacuo, residue is hydroxyl
Tyrosol extract.
Preferably, step（2）Extraction be to be carried out in Soxhlet extraction device.
Preferably, step（2）In, the solid-liquid ratio of the useless cake of olive and n-hexane is 1-5 g：100 mL.
Preferably, step（4）In, mixed acetic acid ethyl acetate extract is evaporated in vacuo in a rotary evaporator to 37
℃。
The beneficial effects of the invention are as follows：The present invention carries out the preparation of hydroxytyrosol using olive waste, obtains hydroxytyrosol
Have the function of anti-oxidant etc., can be adapted for skin resisting oxidation and delaying senility purposes.
Description of the drawings：
Fig. 1 is the collection of illustrative plates and peak area of the HPLC of hydroxytyrosol standard items.
Fig. 2 is the collection of illustrative plates and peak area of the HPLC of the hydroxytyrosol of extraction.
Fig. 3 is the ORAC results of the hydroxytyrosol of extraction.
Specific implementation mode
With reference to embodiment, the present invention is described in further detail, but does not constitute and appoint to the present invention
What limit, anyone within the scope of the invention as claimed made by limited number of time change, still the present invention claim protect
It protects in range.
Embodiment 1
The olive cake that gives up is put into freeze drier and is freeze-dried, dried olive cake is taken out after 12h.
The useless cake of the dried olives of 2.5g is weighed, is extracted using Soxhlet extraction device, with 250mL n-hexane extraction olives
The useless cake of olive 60 minutes, to carry out fatty removal.
Degreasing extract is weighed, is hydrolyzed with NaOH, and with 250rpm stirrings 88 minutes in orbit shaker, then
Hydrolysate is acidified to pH3 with dense HCl, obtains clear solution.Clear solution 10mL ethyl acetate is extracted seven times.It will mixing
Acetic acid ethyl acetate extract be evaporated in vacuo in a rotary evaporator to 37 DEG C.Dry residue is dissolved in the aqueous solution of 10mL
For the detection of hydroxytyrosol and quantitative.
With chromatographic column C18 columns（150 × 4.6mm, 5um）, 30 DEG C of column temperature, acetonitrile：Water=15：85（0.2% glacial acetic acid）For stream
Dynamic phase, sample size 10ul, wavelength 280nm, flow velocity 0.8mL/min in carrying out efficiently, with l distillation water dissolutions and constant volume, obtain concentration
For the reference substance solution of 1mg/mL, then it is drawn respectively 0.1,0.2,0.3,0.4,0.5mL in 10mL volumetric flasks, obtain concentration
It is the reference substance solution of 10,20,30,40,50ug/ mL.Using hydroxytyrosol area as ordinate Y, with a concentration of cross of hydroxytyrosol
Coordinate X（ug/ mL）Linear regression is carried out, it is Y=41122.8x, R to obtain regression equation2=0.992.By the sample of hydroxytyrosol
Sample introduction is carried out, by measuring its a concentration of 3.35ug/ mL, it is 1.34% to calculate and obtain the yield of hydroxytyrosol.
The hydroxytyrosol of acquisition is subjected to determination oxidative, by hydroxytyrosol sample according to 8mg/kg, 16mg/kg's
Dosage is oral to be fed for mouse, after persistently feeding 2 weeks, takes its antioxidant ability index of its blood measuring（ORAC）, while with identical dose
The Vc of amount is compared, as a result, it has been found that feeding ORAC in the blood of hydroxytyrosol（Oxygen radical absorbability）It is feed Vc 13 times
Left and right（Fig. 3）.
The above experimental result may indicate that：The present invention prepares hydroxytyrosol, and the hydroxyl extracted in capable of giving up cake from olive
Tyrosol has anti-oxidation function.
Claims (4)
1. the extracting method of hydroxytyrosol, includes the following steps in olive oil processing waste：
（1）The olive cake that gives up is freeze-dried；
（2）It takes dried olive to give up cake, n-hexane extraction, removal fat is added；
（3）Take step（2）Obtained degreasing product is added NaOH and is hydrolyzed, hydrolysate is then acidified to pH3- with HCl
4, obtain clear solution；
（4）Clear solution is extracted with ethyl acetate, mixed acetic acid ethyl acetate extract is evaporated in vacuo, residue is hydroxyl
Tyrosol extract.
2. extracting method according to claim 1, which is characterized in that step（2）Extraction be in Soxhlet extraction device
It carries out.
3. extracting method according to claim 1, which is characterized in that step（2）In, the feed liquid of olive useless cake and n-hexane
Than for 1-5 g：100 mL.
4. extracting method according to claim 1, which is characterized in that step（4）In, mixed acetic acid ethyl acetate extract is
It is evaporated in vacuo in a rotary evaporator to 37 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810032952.XA CN108285407A (en) | 2018-01-13 | 2018-01-13 | The extracting method of hydroxytyrosol in olive oil processing waste |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810032952.XA CN108285407A (en) | 2018-01-13 | 2018-01-13 | The extracting method of hydroxytyrosol in olive oil processing waste |
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| Publication Number | Publication Date |
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| CN108285407A true CN108285407A (en) | 2018-07-17 |
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| CN201810032952.XA Pending CN108285407A (en) | 2018-01-13 | 2018-01-13 | The extracting method of hydroxytyrosol in olive oil processing waste |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110302121A (en) * | 2019-08-16 | 2019-10-08 | 澳思美日用化工（广州）有限公司 | A kind of baby's diaper ointment and preparation method thereof containing plant essence |
| CN112342258A (en) * | 2019-08-08 | 2021-02-09 | 陈徉 | Method for synchronously separating olive kernel oil and preparing antioxidant peptide |
| CN112617198A (en) * | 2020-12-24 | 2021-04-09 | 常州市芙丽佳生物科技有限公司 | Preparation method of olive kernel extract |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101784205A (en) * | 2007-08-21 | 2010-07-21 | 帝斯曼知识产权资产管理有限公司 | Method of making distilled olive juice extracts |
| CN103113195A (en) * | 2013-03-06 | 2013-05-22 | 中国林业科学研究院林产化学工业研究所 | Novel method for rapidly preparing hydroxytyrosol |
-
2018
- 2018-01-13 CN CN201810032952.XA patent/CN108285407A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101784205A (en) * | 2007-08-21 | 2010-07-21 | 帝斯曼知识产权资产管理有限公司 | Method of making distilled olive juice extracts |
| CN103113195A (en) * | 2013-03-06 | 2013-05-22 | 中国林业科学研究院林产化学工业研究所 | Novel method for rapidly preparing hydroxytyrosol |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112342258A (en) * | 2019-08-08 | 2021-02-09 | 陈徉 | Method for synchronously separating olive kernel oil and preparing antioxidant peptide |
| CN110302121A (en) * | 2019-08-16 | 2019-10-08 | 澳思美日用化工（广州）有限公司 | A kind of baby's diaper ointment and preparation method thereof containing plant essence |
| CN110302121B (en) * | 2019-08-16 | 2022-04-26 | 澳思美日用化工（广州）有限公司 | Infant hip-protecting cream containing plant essence and preparation method thereof |
| CN112617198A (en) * | 2020-12-24 | 2021-04-09 | 常州市芙丽佳生物科技有限公司 | Preparation method of olive kernel extract |
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Application publication date: 20180717 |
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