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Glycyrrhizic AcidGlycyrrhizic Acid
(E number : E958)
Piyusha PatilPiyusha Patil
13FET101213FET1012
INTRODUCTION TO GLYCYRRHIZAINTRODUCTION TO GLYCYRRHIZA
 Common name:Common name: Liquorice, Sweet Wood,
Regolizia (Italian), Jethimadh, Yastimadhu
 Biological sources:Biological sources:
It is obtained from the dried, unpeeled, roots
and stolons of Glycyrrhiza glabra.
 FamilyFamily:: Leguminosae
 Part used:Part used: Roots & Stolons
 Geographical Source:Geographical Source: commercially
cultivated in Spain, Sicily and England.
 Allied species:Allied species: Glycyrrhiza uralensis
CHEMICAL CONSTITUENTSCHEMICAL CONSTITUENTS
• Chief constituent of Liquorice-Chief constituent of Liquorice- Glycyrrhizin.
• Glycyrrhizin:Glycyrrhizin:
 A triterpenoidal saponin glycoside.
 Also called Glycyrrhizic acid or Glycyrrhizinic acid.
 Present in nature as potassium and calcium salt.
 Licorice also contains flavonoids, reducing and non-reducing
sugars, nitrogenous constituents, starch , esential oils, etc.
 20 % water soluble extracts of which 3-5 % is glycyrrhizin.
 Glycyrrhizin is available in various forms : calcium glycyrrhizin,
disodium glycyrrhizinate, monoammonium glycyrrhizinate,
potassium glycyrrhizinate and magnesium glycyrrhizinate,
ammonium glycyrrhizin.
Being a glycoside, Glycyrrhizic acid, on hydrolysis gives an aglycone
and a glycone portions:
• Glycyrrhizinic acidGlycyrrhizinic acid Glycrrhetinic acid (Glycyrrhetic acid),Glycrrhetinic acid (Glycyrrhetic acid),
which is an aglycone of triterpenoidal structure + 2 moles of
Gluconic acid.
• Upon hydrolysis, the glycoside loses its sweet taste.sweet taste.   
CHEMICAL STRUCTURECHEMICAL STRUCTURE
Glycyrrhizic acid
Glycyrrhetinic acid
STRUCTURALLY & CHEMICALLY SIMILAR TO ALDOSTERONE &
DESOXYCORTICOSTERONE
GLYCYRRHIZGLYCYRRHIZ
ININ
PROPERTIESPROPERTIES
• GlycyrrhizinGlycyrrhizin is the main sweet tasting compound from liquorice root. As a natural
sweetener, slow to taste, but taste long-lasting; leaves strong, lingering licorice-
like aftertaste.
• It is 30–50 times as sweet as sucrose with zero glycemic index. Ammoniated salt
approximately 50 to 100 times sweeter than sucrose. Shows synergistic effect
with sucrose i.e. 100 times sweeter.
• Pure glycyrrhizin is odorless.
• Ammonium glycyrrhizine (AG):Ammonium glycyrrhizine (AG): spray-dried brown powder; monoammoniummonoammonium
glycyrrhizin (MAG):glycyrrhizin (MAG): white crystalline powder.
• Glycyrrhizin and other products with this component have a long history of
medicinal value and are used in the treatment of peptic ulcer, especially
glycyrrhetinic acid (triterpene derivative).
• IUPAC NameIUPAC Name::
(3β,18α)-30-hydroxy-11,30-dioxoolean-12-en-3-yl 2-O-β-D-
glucopyranuronosyl-β-D-glucopyranosiduronic acid.
• Molecular formula:Molecular formula:
 Ammonium glycyrrhizinate pentahydrate: C42H65NO16 5H2O (molecular weight 930.04)
 Monoammonium glycyrrhizin: C42H61O16NH4 5H2O
 Glycyrrhizic acid: C46H62O16
 Dipotassium glycyrrhizin: C42H60K2O16
• Molecular weightMolecular weight:: 822.94gm/mol (GA).
• Solubility:Solubility: Freely soluble in hot water, alcohol; slightly soluble in ether.
However, its ammonium salt is soluble in water. Ammonium glycyrrhizin
gets inactivated in the acidic medium (< pH 4.5 ) due to precipitation of
the acid.
• Relatively heat stable but deteriorates above 150 C. Ammonium̊
glycyrrhizinate pentahydrate: decomposes at 212–217.
ExtractionExtraction
1.1. Licorice (glycyrrhiza) rootLicorice (glycyrrhiza) root is the dried and ground rhizome and root
portions of Glycyrrhiza glabra or other species of Glycyrrhiza. Licorice
extract is that portion of the licorice root that is, after maceration,
extracted by boiling water. The extract can be further purified by
filtration and by treatment with acids and ethyl alcohol. Licorice
extract is sold as a liquid, paste (block), or spray-dried powder.
Licorice paste is preferred for flavoring purposes whereas the
powdered licorice is used in confectioneries and pharmaceutical
products.
2. Ammoniated glycyrrhizin2. Ammoniated glycyrrhizin is prepared from the water extract of
licorice root by acid precipitation followed by neutralisation with
dilute ammonia.
LEGISLATION:LEGISLATION:
1.1. USA:USA:
• GRAS flavouring agent but not as a sweetner.
• Upper limit of consumption : 100mg / day
• In Japan , glycyrrhizin is used as a sweetner in combination with
another plant based sweetner like stevia.
2.2. UK and EUROPE:UK and EUROPE:
FEMA:
• No. 2630 (root)
• No. 2628 (extract)
• No. 2629 (extract powder)
• No. 2528 (ammoniated salt).
• Non-calorific.Non-calorific.
• Poisonous by intravenous route.
• Moderately toxic by ingestion and intraperitoneal routes; human systemic
effects by ingestion.
• TCSATCSA (Toxic Substance Control Act) Listed.
• Heated to decomposition will emit acrid smoke and irritating fumes. Adverse
effect of hypermineralocorticoidism from excessive intake.
• Various genotoxic studies have indicated that glycyrrhizin is neitherneither
teratogenic nor mutagenic.teratogenic nor mutagenic.
Food Safety and ToxicityFood Safety and Toxicity
Food ApplicationsFood Applications
• FUNCTION IN FOODS:FUNCTION IN FOODS:
Foaming agent; nutritive sweetener; aromatisation; foam stabiliser;
sweetener; flavour enhancer in foods and confectionery.
• FOOD USE:FOOD USE:
 Baked goods,
 Dairy products (frozen dairy desserts),
 Fruit, vegetables and nut products (hydrolysed vegetable protein (HVP), bean paste),
 Beverages (non-alcoholic beverages) & Soft drinks (root beer),
 Sugars, sugar preserves and confectionery (confectionery manufacture, soft candy,
confection, frosting, hard candy),
 Alcoholic drinks (liqueurs) & Vinegar,
 Pickles and sauces (soy sauce),
 Other (tobacco, chocolate, vanilla, medicines, gelatin, pudding, chewing gum).
• The ingredient is not permitted to be used as a non-nutritive
sweetener in sugar substitutes. Has less applications as a sweetener.
• Foaming agentFoaming agent in some non-alcoholic beverages.
• Uses as a flavor enhancer:Uses as a flavor enhancer:
 Baked foods, Alcoholic beverages, Chewing gum.
• Mostly used in tobacco and pharma.
Health BenefitsHealth Benefits
• Licorice is used for various digestive system complaints including stomach ulcers,
heartburn, colic, and ongoing inflammation of the lining of the stomach (chronic gastritis).(chronic gastritis).
• Some people use licorice for sore throat, bronchitis, cough,sore throat, bronchitis, cough, and infections caused by bacteria
or viruses.
• Licorice is also used for osteoarthritis, systemic lupus erythematosus SLE), liver
disorders, malaria, tuberculosis, food poisoning, and chronic fatigue syndrome (CFS).(CFS).
• Licorice is sometimes used along with the herbs Panax ginseng and Bupleurum falcatumherbs Panax ginseng and Bupleurum falcatum to
improve the function of the adrenal glands, especially in people who have taken steroid drugs
long-term. Steroids tend to suppress the activity of the adrenal glands. The adrenal glands
produce important hormones that regulate the body’s response to stress.
• Licorice is also used in an herbal form called Shakuyaku-kanzo-to to increase fertility in womenfertility in women
with a hormonal disorder called polycystic ovary syndrome.polycystic ovary syndrome. In combination with other herbs,
licorice is also used to treat prostate cancer and the skin disorderprostate cancer and the skin disorder known as eczema.eczema.
• Some people use licorice as a shampoo to reduce oiliness in their hair.hair.
• It is an expectorent and hence is used extensively in cough syrups.
• Licorice interacts with many prescription medicines.
• Glycyrrhizin inhibits liver cell injuryinhibits liver cell injury caused by many chemicals and is used in the
treatment of chronic hepatitis and cirrhosis in Japan.
• It also inhibits the growth of several DNA and RNA virusesinhibits the growth of several DNA and RNA viruses, inactivating herpes
simplex virus particles irreversibly.  The Glycyrrhizin acid blocks the first steps on viral
replication as well as the viron exit from the capside.
• The compositions of licorice root containing glycyrrhizin have been reported to decreasedecrease
serum testosterone levels in malesserum testosterone levels in males (the active component of licorice, glycyrrhizic acid
interferes with the enzyme which catalyzes the conversion of androstenedione to
testosterone).
• Studies also have demonstrated that glycyrrhizin inhibits an enzyme that normally
inactivates cortisolcortisol, so that consumption of licorice or glycyrrhizin in excess can raise the
level of cortisol in the body above normal levels. Cortisol has anti-inflammatory
properties, so glycyrrhizin can be beneficial in treating some conditions, but excessive
cortisol can cause water retention, hypertension, and loss of potassium and calcium. 
• Side effects : Edema (water retention ) and hypertension.
ConclusionConclusion
• It has very less applications as a sweetener, but used as aIt has very less applications as a sweetener, but used as a
flavoring agent quite often.flavoring agent quite often.
• It is still being extensively used and is under research toIt is still being extensively used and is under research to
optimize its use.optimize its use.
Thank You!Thank You!

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13 fet1012 glycyrrhizic acid

  • 1. Glycyrrhizic AcidGlycyrrhizic Acid (E number : E958) Piyusha PatilPiyusha Patil 13FET101213FET1012
  • 2. INTRODUCTION TO GLYCYRRHIZAINTRODUCTION TO GLYCYRRHIZA  Common name:Common name: Liquorice, Sweet Wood, Regolizia (Italian), Jethimadh, Yastimadhu  Biological sources:Biological sources: It is obtained from the dried, unpeeled, roots and stolons of Glycyrrhiza glabra.  FamilyFamily:: Leguminosae  Part used:Part used: Roots & Stolons  Geographical Source:Geographical Source: commercially cultivated in Spain, Sicily and England.  Allied species:Allied species: Glycyrrhiza uralensis
  • 3. CHEMICAL CONSTITUENTSCHEMICAL CONSTITUENTS • Chief constituent of Liquorice-Chief constituent of Liquorice- Glycyrrhizin. • Glycyrrhizin:Glycyrrhizin:  A triterpenoidal saponin glycoside.  Also called Glycyrrhizic acid or Glycyrrhizinic acid.  Present in nature as potassium and calcium salt.  Licorice also contains flavonoids, reducing and non-reducing sugars, nitrogenous constituents, starch , esential oils, etc.  20 % water soluble extracts of which 3-5 % is glycyrrhizin.  Glycyrrhizin is available in various forms : calcium glycyrrhizin, disodium glycyrrhizinate, monoammonium glycyrrhizinate, potassium glycyrrhizinate and magnesium glycyrrhizinate, ammonium glycyrrhizin.
  • 4. Being a glycoside, Glycyrrhizic acid, on hydrolysis gives an aglycone and a glycone portions: • Glycyrrhizinic acidGlycyrrhizinic acid Glycrrhetinic acid (Glycyrrhetic acid),Glycrrhetinic acid (Glycyrrhetic acid), which is an aglycone of triterpenoidal structure + 2 moles of Gluconic acid. • Upon hydrolysis, the glycoside loses its sweet taste.sweet taste.   
  • 5. CHEMICAL STRUCTURECHEMICAL STRUCTURE Glycyrrhizic acid Glycyrrhetinic acid STRUCTURALLY & CHEMICALLY SIMILAR TO ALDOSTERONE & DESOXYCORTICOSTERONE
  • 7. PROPERTIESPROPERTIES • GlycyrrhizinGlycyrrhizin is the main sweet tasting compound from liquorice root. As a natural sweetener, slow to taste, but taste long-lasting; leaves strong, lingering licorice- like aftertaste. • It is 30–50 times as sweet as sucrose with zero glycemic index. Ammoniated salt approximately 50 to 100 times sweeter than sucrose. Shows synergistic effect with sucrose i.e. 100 times sweeter. • Pure glycyrrhizin is odorless. • Ammonium glycyrrhizine (AG):Ammonium glycyrrhizine (AG): spray-dried brown powder; monoammoniummonoammonium glycyrrhizin (MAG):glycyrrhizin (MAG): white crystalline powder. • Glycyrrhizin and other products with this component have a long history of medicinal value and are used in the treatment of peptic ulcer, especially glycyrrhetinic acid (triterpene derivative).
  • 8. • IUPAC NameIUPAC Name:: (3β,18α)-30-hydroxy-11,30-dioxoolean-12-en-3-yl 2-O-β-D- glucopyranuronosyl-β-D-glucopyranosiduronic acid. • Molecular formula:Molecular formula:  Ammonium glycyrrhizinate pentahydrate: C42H65NO16 5H2O (molecular weight 930.04)  Monoammonium glycyrrhizin: C42H61O16NH4 5H2O  Glycyrrhizic acid: C46H62O16  Dipotassium glycyrrhizin: C42H60K2O16 • Molecular weightMolecular weight:: 822.94gm/mol (GA). • Solubility:Solubility: Freely soluble in hot water, alcohol; slightly soluble in ether. However, its ammonium salt is soluble in water. Ammonium glycyrrhizin gets inactivated in the acidic medium (< pH 4.5 ) due to precipitation of the acid. • Relatively heat stable but deteriorates above 150 C. Ammonium̊ glycyrrhizinate pentahydrate: decomposes at 212–217.
  • 9. ExtractionExtraction 1.1. Licorice (glycyrrhiza) rootLicorice (glycyrrhiza) root is the dried and ground rhizome and root portions of Glycyrrhiza glabra or other species of Glycyrrhiza. Licorice extract is that portion of the licorice root that is, after maceration, extracted by boiling water. The extract can be further purified by filtration and by treatment with acids and ethyl alcohol. Licorice extract is sold as a liquid, paste (block), or spray-dried powder. Licorice paste is preferred for flavoring purposes whereas the powdered licorice is used in confectioneries and pharmaceutical products. 2. Ammoniated glycyrrhizin2. Ammoniated glycyrrhizin is prepared from the water extract of licorice root by acid precipitation followed by neutralisation with dilute ammonia.
  • 10. LEGISLATION:LEGISLATION: 1.1. USA:USA: • GRAS flavouring agent but not as a sweetner. • Upper limit of consumption : 100mg / day • In Japan , glycyrrhizin is used as a sweetner in combination with another plant based sweetner like stevia. 2.2. UK and EUROPE:UK and EUROPE: FEMA: • No. 2630 (root) • No. 2628 (extract) • No. 2629 (extract powder) • No. 2528 (ammoniated salt).
  • 11. • Non-calorific.Non-calorific. • Poisonous by intravenous route. • Moderately toxic by ingestion and intraperitoneal routes; human systemic effects by ingestion. • TCSATCSA (Toxic Substance Control Act) Listed. • Heated to decomposition will emit acrid smoke and irritating fumes. Adverse effect of hypermineralocorticoidism from excessive intake. • Various genotoxic studies have indicated that glycyrrhizin is neitherneither teratogenic nor mutagenic.teratogenic nor mutagenic. Food Safety and ToxicityFood Safety and Toxicity
  • 12. Food ApplicationsFood Applications • FUNCTION IN FOODS:FUNCTION IN FOODS: Foaming agent; nutritive sweetener; aromatisation; foam stabiliser; sweetener; flavour enhancer in foods and confectionery. • FOOD USE:FOOD USE:  Baked goods,  Dairy products (frozen dairy desserts),  Fruit, vegetables and nut products (hydrolysed vegetable protein (HVP), bean paste),  Beverages (non-alcoholic beverages) & Soft drinks (root beer),  Sugars, sugar preserves and confectionery (confectionery manufacture, soft candy, confection, frosting, hard candy),  Alcoholic drinks (liqueurs) & Vinegar,  Pickles and sauces (soy sauce),  Other (tobacco, chocolate, vanilla, medicines, gelatin, pudding, chewing gum).
  • 13. • The ingredient is not permitted to be used as a non-nutritive sweetener in sugar substitutes. Has less applications as a sweetener. • Foaming agentFoaming agent in some non-alcoholic beverages. • Uses as a flavor enhancer:Uses as a flavor enhancer:  Baked foods, Alcoholic beverages, Chewing gum. • Mostly used in tobacco and pharma.
  • 14. Health BenefitsHealth Benefits • Licorice is used for various digestive system complaints including stomach ulcers, heartburn, colic, and ongoing inflammation of the lining of the stomach (chronic gastritis).(chronic gastritis). • Some people use licorice for sore throat, bronchitis, cough,sore throat, bronchitis, cough, and infections caused by bacteria or viruses. • Licorice is also used for osteoarthritis, systemic lupus erythematosus SLE), liver disorders, malaria, tuberculosis, food poisoning, and chronic fatigue syndrome (CFS).(CFS). • Licorice is sometimes used along with the herbs Panax ginseng and Bupleurum falcatumherbs Panax ginseng and Bupleurum falcatum to improve the function of the adrenal glands, especially in people who have taken steroid drugs long-term. Steroids tend to suppress the activity of the adrenal glands. The adrenal glands produce important hormones that regulate the body’s response to stress. • Licorice is also used in an herbal form called Shakuyaku-kanzo-to to increase fertility in womenfertility in women with a hormonal disorder called polycystic ovary syndrome.polycystic ovary syndrome. In combination with other herbs, licorice is also used to treat prostate cancer and the skin disorderprostate cancer and the skin disorder known as eczema.eczema. • Some people use licorice as a shampoo to reduce oiliness in their hair.hair. • It is an expectorent and hence is used extensively in cough syrups. • Licorice interacts with many prescription medicines.
  • 15. • Glycyrrhizin inhibits liver cell injuryinhibits liver cell injury caused by many chemicals and is used in the treatment of chronic hepatitis and cirrhosis in Japan. • It also inhibits the growth of several DNA and RNA virusesinhibits the growth of several DNA and RNA viruses, inactivating herpes simplex virus particles irreversibly.  The Glycyrrhizin acid blocks the first steps on viral replication as well as the viron exit from the capside. • The compositions of licorice root containing glycyrrhizin have been reported to decreasedecrease serum testosterone levels in malesserum testosterone levels in males (the active component of licorice, glycyrrhizic acid interferes with the enzyme which catalyzes the conversion of androstenedione to testosterone). • Studies also have demonstrated that glycyrrhizin inhibits an enzyme that normally inactivates cortisolcortisol, so that consumption of licorice or glycyrrhizin in excess can raise the level of cortisol in the body above normal levels. Cortisol has anti-inflammatory properties, so glycyrrhizin can be beneficial in treating some conditions, but excessive cortisol can cause water retention, hypertension, and loss of potassium and calcium.  • Side effects : Edema (water retention ) and hypertension.
  • 16. ConclusionConclusion • It has very less applications as a sweetener, but used as aIt has very less applications as a sweetener, but used as a flavoring agent quite often.flavoring agent quite often. • It is still being extensively used and is under research toIt is still being extensively used and is under research to optimize its use.optimize its use.