Title of Invention	A PROCESS FOR THE ISOLATION OF ARONATIC TURMERONE OIL FROM TURMERIC OLEORESIN INDUSTRY WASTE
Abstract	A process for the isolation of aromatic Turmerone oil from turmeric oleoresin industry waste by extracting the turmeric oil from curcumin free turmeric oleoresin by using a non-polar solvent, filtrating and vacuum drying the extract subsequently re-extracting the residue obtained from the previous extract by the same non polar solvent to obtain the second extract and third extract, concentrating the above combined extract characterized in that by using distillation to obtain the crude turmeric oil followed by fractional vacuum distillation to obtain the two aromatic fractions fraction 1 and fraction 2 aromatic termerone enriched turmeric oil.

Title of Invention

A PROCESS FOR THE ISOLATION OF ARONATIC TURMERONE OIL FROM TURMERIC OLEORESIN INDUSTRY WASTE

Abstract

A process for the isolation of aromatic Turmerone oil from turmeric oleoresin industry waste by extracting the turmeric oil from curcumin free turmeric oleoresin by using a non-polar solvent, filtrating and vacuum drying the extract subsequently re-extracting the residue obtained from the previous extract by the same non polar solvent to obtain the second extract and third extract, concentrating the above combined extract characterized in that by using distillation to obtain the crude turmeric oil followed by fractional vacuum distillation to obtain the two aromatic fractions fraction 1 and fraction 2 aromatic termerone enriched turmeric oil.

Full Text	The present invention relates to a process for the isolation of Ar. Turmerone oil from turmeric oleoresin industry waste. In particular the process involves isolation of turmeric oil enriched with Aromatic Turmerone, from a byproduct of Turmeric oleoresin Industry. Ar. turmerone [(S)-2-methyl-6-(4-methylphenyl)-2-hepten-4-one] is the major sesquiterpene found in turmeric oil. Ar. turmerone has potential as an antivenom agent. It has been shown that Ar. turmerone neutralizes both the hemorrhagic activity present in Bothrous jararaca venom and the lethal effect of Crolalus durissus tarrifius venom in mice (Ferreira et al., Toxicon 30, 1211, 1992). Ar. turmerone is also used in insect repellent coatings (Whalon et al, US 000835378, 1998; Su et al, J. Agric. Food Chen 30, 290, 1982) and have mosquitocidal activity (Roth et al, J. Nat. Prod. 61, 542, 1998). The cytotoxicity potentiating substaace was identified as (+) Ar. Turmerone. Turmerone potentiated the cytotoxicity of p-sesquiphellandrene (5 fold), Me CCNO (10 fold) and cyclophosphamide (10 fold) (Khanna, Current Science, 76, 1351, 1999). Curcumin is industrially produced using oleoresin of turmeric as the starting material. The mother liquor, curcumin removed turmeric oleoresin has a composition of oil, resin and unisolable curcumin and it has no commercial value at present. This has a little demand in the perfume industry and is mostly used for boiler fuel as it is waste in the process of curcumin extraction (Saju et al, Current Sci. 75, 660, 1998). The major compounds present in turmeric oil are identified as p-cymene,ß-sesquiphellandrene, turmerone, Ar-turmerone, sesquiterpene hydrocarbons and sesqueterpene alcohols. Govindarajan (CRC Critical Rev. Food Sci. Nutr. 12, 199, 1980) reported the presence of limonene, cineole, citral, Ar-curcumene, zingiberene, p-sesquiphelandrene and bisabolene as minor components and Ar-turmerone and turmerone as major comounds. Negi et al. has reported antimicrobial activity of turmeric oil (J. Agric. Food Chem. 47, 4297, 1999). Turmeric oil is an effective inhibitor of 5-lipoxygenase, cyclooxygenses, lukotriene biosynthesis, lipid peroxidation and AOS scavenger. Turmeric oil is an effective mosquito repellent and compares favourably with dimethyl phthalate in its repellent action against mosquitoes, the time of protection being 282 min comapred to 240 for dimethyl phthalate. It has a quick knockdown effect on housefly (Musca nebule) nearly comparable with Lethane 384 and Thanite. Turmeronol A and B have recently been isolated from Curcuman longa and characterized as novel inhibitors of soybean lipoxygenase (Takeshi Kitahara et al. Bioscience, Biotechnology and Biochemistry, 57, 1137, 1993). Literature survey showed that, there is no report on the enrichment of Ar. turmerone in turmeric oil. Hence, we have developed a process for enriching Ar. turmerone from turmeric oleoresin industry waste. The main object of the present invention is to provide a process for enriching Ar. turmerone from turmeric oleoresin industry waste. Another object of the present invention is to utilise the byproduct of turmeric oleoresin industries. Accordingly the present invention provides a process for the isolation of aromatic Turmerone oil from turmeric oleoresin industry waste which comprises extracting the turmeric oil from curcumin free turmeric oleoresin by using a non-polar solvent, filtrating and vacuum drying the extract subsequently re-extracting the residue obtained from the previous extract by the same non polar solvent to obtain the second extract and third extract, concentrating the above combined extract by distillation to obtain the crude turmeric oil followed by fractional vacuum distillation to obtain the two aromatic fractions fraction 1 and fraction 2 aromatic termerone enriched turmeric oil. In an embodiment of the present invention the non polar solvent used is selected from hexane and petroleum ether. In an another embodiment of the present invention the two fractions are collected under vacuum at different temperature. In yet another embodiment of the fractions I and II gave 10-11% and 15-16% yield, respectively. In yet another embodiment of the fraction I and II were analysed by known methods and they contained 3-6% and 62-74% of aromatic turmerone, respectively. The enrichment of Ar. Turmerone was done according to following flow diagram By-product from oleoresin industry (Figure Removd) Extraction at 20-60° CDistillation at 60°C Turmeric oil (40-60 %) Fractional Vacuum Distillation 25mm Residue GC conditions (Table Removed) GC-MS conditions (Table Removed) The novelty of this process is that the method for obtaining turmeric oil enriched with Ar. turmerone was devloped for the first time. The method of recovering turmeric oil from turmeric oleoresin industry waste and enriching it with Ar. turmerone can bring value addition to turmeric oleoresin Industry. The following examples are given by way of illustrations of the present invention and therefore should not be constructed to limit the scope of the present invention. Example-1. 1000 g of curcumin removed turmeric oleoresin was taken in 5 liters glass beaker and 2000 ml of hexane was added to it with continuous stirring for 25 min at 25 °C and filtered through filter paper. The residue (725 g) was re-extracted with 1500 ml of hexane for 25 min at 25 °C and filtered through filter paper. The residue (610 g) was further extracted with 1200 ml of hexane for 25 min at 25 °C and filtered through filter paper. The residue (540 g) was further extracted with 1000 ml of hexane for 25 min at 25 °C and filtered through filter paper. All the extracts were combined. The combined extract (6200 ml) was concentrated by distillation to recover the hexane and it yielded 510 ml of crude turmeric oil. 200 ml of crude turmeric oil was subjected to fractional vacuum distillation. First fraction was drawn starting at 100°C vapour temperature and collected until the vapour temperature reached 120 °C under 25 mm vacuum. The yield of first fraction was 11% with respect to crude turmeric oil. Similarly collection of second fraction was started at 121 °C vapour temperature and continued upto 150°C vapour temperature under 25 mm vacuum. The yield of second fraction was 16% with respect to crude turmeric oil. Fraction I and II were analysed by known methods and their Ar. turmerone content was 3 and 73.93%, respectively. The turmeric oil containing 73.93% Ar. turmerone at 50 ppm was sufficient for complete inhibition of B. subtilis and S. aureus, whereas turmeric oil containing 41.36% Ar. turmerone inhibited these organisms completely at 100 ppm. In case of B. coagulans at 25 ppm 53.6% inhibition was observed for turmeric oil containing 73.93% Ar. turmerone and 32.6% for turmeric oil containing 62.0% Ar. turmerone. The growth of E. coli and P. aeruginosa was inhibited completely at 200 ppm of turmeric oil containing 77.85% Ar. turmerone, whereas the percentage of inhibition were 35% and 67%, respectively, at the same concentration of the turmeric oil containing 72.0% Ar. turmerone. Example-2. 500 g of curcumin removed turmeric oleoresin was taken in 3 liters round bottom flask and 1000 ml of petroleum ether was added to it. It was refluxed for 15 min at 60 °C, cooled to 30 °C and filtered through filter paper. The residue (325 g) was again refluxed with 750 ml of petroleum ether for 15 min at 65 °C, cooled to 30 °C and filtered through filter paper. Both the extracts were combined. The combined extract (1900 ml) was concentrated by distillation to recover the petroleum ether and it yielded 240 ml of crude turmeric oil. 200 ml of crude turmeric oil was subjected to fractional vacuum distillation. First fraction was drawn starting at 100°C vapour temperature and collected until the vapour temperature reached 120 °C under 25 mm vacuum. The yield of first fraction was 10% with respect to crude turmeric oil. Similarly collection of second fraction was started at 121 °C vapour temperature and continued upto 150°C vapour temperature under 25 mm vacuum. The yield of second fraction was 15.5% with respect to crude turmeric oil. Fraction I and II were analyzed by known methods and their Ar. turmerone content was 5.6 and 62.3%, respectively. The turmeric oil containing 73.93% Ar. turmerone brought about complete inhibition of Bacillus subtilis and B. coagulens growth at 50 ppm whereas at the same level turmeric oil containing 41.36% Ar. turmerone growth inhibition for same bacteria was 52.7% and 62.4%, respectively. The turmeric oil containing 62.0% Ar. turmerone inhibited complete growth of B. coagulens at 50 ppm, whereas the growth inhibition was only 62.4% in case of turmeric oil containing 41.36% Ar. turmerone at same concentration. Example-3. 400 g of curcumin removed turmeric oleoresin was taken in 3 liters glass beaker and 1200 ml of hexane was added to it with continuous stirring for 15 min at 30 °C and filtered through filter paper. The residue (310 g) was re-extracted with 900 ml of hexane for 15 min at 30 °C and filtered through filter paper. The residue (265 g) was further extracted with 750 ml of hexane for 15 min at 30 °C and filtered through filter paper. All the extracts were combined. The combined extract (3050 ml) was concentrated by distillation to recover the hexane and it yielded 208 ml of crude turmeric oil. 208 ml of crude turmeric oil was subjected to fractional vacuum distillation. First fraction was drawn starting at 100°C vapour temperature and collected until the vapour temperature reached 120 °C under 25 mm vacuum. The yield of first fraction was 10.2% with respect to crude turmeric oil. Similarly collection of second fraction was started at 121°C vapour temperature and continued upto 150°C vapour temperature under 25 mm vacuum. The yield of second fraction was 15.1% with respect to crude turmeric oil. Fraction I and II were analyzed by known methods and their Ar. turmerone content was 3.6 and 62.55%, respectively. The main advantages of the present invention are: 1. A biologically active substance can be obtained from the industrial byproduct. 2. The substance obtained is of natural origin. 3. The substance is highly active against several microorganisms therefore it has application as an antimicrobial agent. We claim: 1. A process for the isolation of aromatic Turmerone oil from turmeric oleoresin industry waste which comprises extracting the turmeric oil from curcumin free turmeric oleoresin by using a non-polar solvent, filtrating and vacuum drying the extract subsequently re-extracting the residue obtained from the previous extract by the same non polar solvent to obtain the second extract and third extract, concentrating the above combined extract characterized in that by using distillation to obtain the crude turmeric oil followed by fractional vacuum distillation to obtain the two aromatic fractions fraction 1 and fraction 2 aromatic termerone enriched turmeric oil. 2. A process as claimed in claim 1 wherein the non polar solvent used is selected from hexane and petroleum ether. 3. A process as claimed in claims 1 & 2 wherein the two fractions are collected under vacuum at 100 to 120°C & 121 to 130°C. 4. A process as claimed in claims 1 to 3 wherein the fractions I and 2 gave 10-11% and 15-16% yield, respectively. 5. A process as claimed in claims 1 to 4 wherein the fraction I and 2 were analysed by known methods and they contained 3-6% and 62-74% of aromatic turmerone, respectively. 6. A process for the isolation of aromatic Turmerone oil from turmeric oleoresin industry waste substantially as herein described with reference to the examples

Full Text

The present invention relates to a process for the isolation of Ar. Turmerone oil from turmeric oleoresin industry waste. In particular the process involves isolation of turmeric oil enriched with Aromatic Turmerone, from a byproduct of Turmeric oleoresin Industry.
Ar. turmerone [(S)-2-methyl-6-(4-methylphenyl)-2-hepten-4-one] is the major sesquiterpene found in turmeric oil. Ar. turmerone has potential as an antivenom agent. It has been shown that Ar. turmerone neutralizes both the hemorrhagic activity present in Bothrous jararaca venom and the lethal effect of Crolalus durissus tarrifius venom in mice (Ferreira et al., Toxicon 30, 1211, 1992). Ar. turmerone is also used in insect repellent coatings (Whalon et al, US 000835378, 1998; Su et al, J. Agric. Food Chen 30, 290, 1982) and have mosquitocidal activity (Roth et al, J. Nat. Prod. 61, 542, 1998). The cytotoxicity potentiating substaace was identified as (+) Ar. Turmerone. Turmerone potentiated the cytotoxicity of p-sesquiphellandrene (5 fold), Me CCNO (10 fold) and cyclophosphamide (10 fold) (Khanna, Current Science, 76, 1351, 1999).
Curcumin is industrially produced using oleoresin of turmeric as the starting material. The mother liquor, curcumin removed turmeric oleoresin has a composition of oil, resin and unisolable curcumin and it has no commercial value at present. This has a little demand in the perfume industry and is mostly used for boiler fuel as it is waste in the process of curcumin extraction (Saju et al, Current Sci. 75, 660, 1998). The major compounds present in turmeric oil are identified as p-cymene,ß-sesquiphellandrene, turmerone, Ar-turmerone, sesquiterpene hydrocarbons and sesqueterpene alcohols. Govindarajan (CRC Critical Rev. Food Sci. Nutr. 12, 199, 1980) reported the presence of limonene, cineole, citral, Ar-curcumene, zingiberene, p-sesquiphelandrene and bisabolene as minor components and Ar-turmerone and turmerone as major comounds. Negi et al. has reported antimicrobial activity of turmeric oil (J. Agric. Food Chem. 47, 4297, 1999). Turmeric oil is an effective inhibitor of 5-lipoxygenase, cyclooxygenses, lukotriene biosynthesis, lipid peroxidation and AOS scavenger. Turmeric oil is an effective mosquito repellent and compares favourably with dimethyl phthalate in its repellent action against mosquitoes, the time of protection being 282 min comapred to 240 for dimethyl phthalate. It has a quick knockdown effect on housefly (Musca nebule) nearly comparable with Lethane 384 and Thanite. Turmeronol A and B have recently

been isolated from Curcuman longa and characterized as novel inhibitors of soybean lipoxygenase (Takeshi Kitahara et al. Bioscience, Biotechnology and Biochemistry, 57, 1137, 1993).
Literature survey showed that, there is no report on the enrichment of Ar. turmerone in turmeric oil. Hence, we have developed a process for enriching Ar. turmerone from turmeric oleoresin industry waste.
The main object of the present invention is to provide a process for enriching Ar. turmerone from turmeric oleoresin industry waste.
Another object of the present invention is to utilise the byproduct of turmeric oleoresin industries.
Accordingly the present invention provides a process for the isolation of aromatic Turmerone oil from turmeric oleoresin industry waste which comprises extracting the turmeric oil from curcumin free turmeric oleoresin by using a non-polar solvent, filtrating and vacuum drying the extract subsequently re-extracting the residue obtained from the previous extract by the same non polar solvent to obtain the second extract and third extract, concentrating the above combined extract by distillation to obtain the crude turmeric oil followed by fractional vacuum distillation to obtain the two aromatic fractions fraction 1 and fraction 2 aromatic termerone enriched turmeric oil.
In an embodiment of the present invention the non polar solvent used is selected from hexane and petroleum ether.
In an another embodiment of the present invention the two fractions are collected under vacuum at different temperature.
In yet another embodiment of the fractions I and II gave 10-11% and 15-16% yield, respectively.
In yet another embodiment of the fraction I and II were analysed by known methods and they contained 3-6% and 62-74% of aromatic turmerone, respectively.
The enrichment of Ar. Turmerone was done according to following flow diagram
By-product from oleoresin industry
(Figure Removd)

Extraction at 20-60° CDistillation at 60°C
Turmeric oil (40-60 %)
Fractional Vacuum Distillation 25mm
Residue GC conditions

(Table Removed)
GC-MS conditions
(Table Removed)
The novelty of this process is that the method for obtaining turmeric oil enriched with Ar. turmerone was devloped for the first time. The method of recovering turmeric oil from turmeric oleoresin industry waste and enriching it with Ar. turmerone can bring value addition to turmeric oleoresin Industry.
The following examples are given by way of illustrations of the present invention and therefore should not be constructed to limit the scope of the present invention.
Example-1.
1000 g of curcumin removed turmeric oleoresin was taken in 5 liters glass beaker and 2000 ml of hexane was added to it with continuous stirring for 25 min at 25 °C and filtered through filter paper. The residue (725 g) was re-extracted with 1500 ml of hexane for 25 min at 25 °C and filtered through filter paper. The residue (610 g) was further extracted with 1200 ml of hexane for 25 min at 25 °C and filtered through filter paper. The residue (540 g) was further extracted with 1000 ml of hexane for 25 min at 25 °C and filtered through filter paper. All the extracts were combined. The combined extract (6200 ml) was concentrated by distillation to recover the hexane and it yielded 510 ml of crude turmeric oil. 200 ml of crude turmeric oil was subjected to fractional vacuum distillation. First fraction was drawn starting at 100°C vapour temperature and collected until the vapour temperature reached 120 °C under 25 mm vacuum. The yield of first fraction was 11% with respect to crude turmeric oil. Similarly collection of second fraction was started at 121 °C vapour temperature and continued upto 150°C vapour temperature under 25 mm vacuum. The yield of second fraction was 16% with respect to crude turmeric oil. Fraction I and II were analysed by known methods and their Ar. turmerone content was 3 and 73.93%, respectively.
The turmeric oil containing 73.93% Ar. turmerone at 50 ppm was sufficient for complete inhibition of B. subtilis and S. aureus, whereas turmeric oil containing 41.36% Ar. turmerone inhibited these organisms completely at 100 ppm. In case of B. coagulans at 25 ppm 53.6% inhibition was observed for turmeric oil containing 73.93% Ar. turmerone and 32.6% for turmeric oil containing 62.0% Ar. turmerone. The growth of E. coli and P. aeruginosa was inhibited completely at 200 ppm of turmeric oil containing 77.85% Ar. turmerone, whereas the percentage of inhibition were 35% and 67%, respectively, at the same concentration of the turmeric oil containing 72.0% Ar. turmerone.
Example-2.
500 g of curcumin removed turmeric oleoresin was taken in 3 liters round bottom flask and 1000 ml of petroleum ether was added to it. It was refluxed for 15 min at 60 °C, cooled to 30 °C and filtered through filter paper. The residue (325 g) was again refluxed with 750 ml of petroleum ether for 15 min at 65 °C, cooled to 30 °C and filtered through filter paper. Both the extracts were combined. The combined extract (1900 ml) was concentrated by distillation to recover the petroleum ether and it yielded 240 ml of crude turmeric oil. 200 ml of crude turmeric oil was subjected to fractional vacuum distillation. First fraction was drawn starting at 100°C vapour temperature and collected until the vapour temperature reached 120 °C under 25 mm vacuum. The yield of first fraction was 10% with respect to crude turmeric oil. Similarly collection of second fraction was started at 121 °C vapour temperature and continued upto 150°C vapour temperature under 25 mm vacuum. The yield of second fraction was 15.5% with respect to crude turmeric oil. Fraction I and II were analyzed by known methods and their Ar. turmerone content was 5.6 and 62.3%, respectively.
The turmeric oil containing 73.93% Ar. turmerone brought about complete inhibition of Bacillus subtilis and B. coagulens growth at 50 ppm whereas at the same level turmeric oil containing 41.36% Ar. turmerone growth inhibition for same bacteria was 52.7% and 62.4%, respectively. The turmeric oil containing 62.0% Ar. turmerone inhibited complete growth of B. coagulens at 50 ppm, whereas the growth inhibition was only 62.4% in case of turmeric oil containing 41.36% Ar. turmerone at same concentration.
Example-3.
400 g of curcumin removed turmeric oleoresin was taken in 3 liters glass beaker and 1200 ml of hexane was added to it with continuous stirring for 15 min at 30 °C and filtered through filter paper. The residue (310 g) was re-extracted with 900 ml of hexane for 15 min at 30 °C and filtered through filter paper. The residue (265 g) was further extracted with 750 ml of hexane for 15 min at 30 °C and filtered through filter paper. All the extracts were combined. The combined extract (3050 ml) was concentrated by distillation to recover the hexane and it yielded 208 ml of crude turmeric oil. 208 ml of crude turmeric oil was subjected to fractional vacuum distillation. First fraction was drawn starting at 100°C vapour temperature and collected until the vapour temperature reached 120 °C under 25 mm vacuum. The yield of first fraction was 10.2% with respect to crude turmeric oil. Similarly collection of second fraction was started at 121°C vapour temperature and continued upto 150°C vapour temperature under 25 mm vacuum. The yield of second fraction was 15.1% with respect to crude turmeric oil. Fraction I and II were analyzed by known methods and their Ar. turmerone content was 3.6 and 62.55%, respectively.
The main advantages of the present invention are:
1. A biologically active substance can be obtained from the industrial byproduct.
2. The substance obtained is of natural origin.
3. The substance is highly active against several microorganisms therefore it has
application as an antimicrobial agent.

We claim:
1. A process for the isolation of aromatic Turmerone oil from turmeric oleoresin
industry waste which comprises extracting the turmeric oil from curcumin free
turmeric oleoresin by using a non-polar solvent, filtrating and vacuum drying the
extract subsequently re-extracting the residue obtained from the previous
extract by the same non polar solvent to obtain the second extract and third
extract, concentrating the above combined extract characterized in that by using
distillation to obtain the crude turmeric oil followed by fractional vacuum
distillation to obtain the two aromatic fractions fraction 1 and fraction 2 aromatic
termerone enriched turmeric oil.
2. A process as claimed in claim 1 wherein the non polar solvent used is selected
from hexane and petroleum ether.
3. A process as claimed in claims 1 & 2 wherein the two fractions are collected
under vacuum at 100 to 120°C & 121 to 130°C.
4. A process as claimed in claims 1 to 3 wherein the fractions I and 2 gave 10-11%
and 15-16% yield, respectively.
5. A process as claimed in claims 1 to 4 wherein the fraction I and 2 were analysed
by known methods and they contained 3-6% and 62-74% of aromatic
turmerone, respectively.
6. A process for the isolation of aromatic Turmerone oil from turmeric oleoresin
industry waste substantially as herein described with reference to the examples

Documents:

215-del-2001-abstract.pdf

215-del-2001-claims.pdf

215-del-2001-correspondence-others.pdf

215-del-2001-correspondence-po.pdf

215-del-2001-description (complete).pdf

215-del-2001-form-1.pdf

215-del-2001-form-19.pdf

215-del-2001-form-2.pdf

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Patent Number

231051

Indian Patent Application Number

215/DEL/2001

PG Journal Number

13/2009

Publication Date

27-Mar-2009

Grant Date

28-Feb-2009

Date of Filing

28-Feb-2001

Name of Patentee

COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

Applicant Address

RAFI MARG, NEW DELHI-110 001, INDIA.

Inventors:

#	Inventor's Name	Inventor's Address
1	GUDDADARANGAVVANAHALLY KRISHNAREDDY JAYAPRAKASHA	CENTRAL FOOD AND TECHNOLOGY RESEARCH INSTITUTE, MYSORE, INDIA.
2	PRADEEP SINGH NEGI	CENTRAL FOOD AND TECHNOLOGY RESEARCH INSTITUTE, MYSORE, INDIA.
3	CHINNASWAMY ANANDHARAMAKRISHNAN	CENTRAL FOOD AND TECHNOLOGY RESEARCH INSTITUTE, MYSORE, INDIA.
4	KUNNUMPURATH KURIAN SAKARIAH	CENTRAL FOOD AND TECHNOLOGY RESEARCH INSTITUTE, MYSORE, INDIA.

PCT International Classification Number

A23D 9/00

PCT International Application Number

N/A

PCT International Filing date

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1			NA