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Carrageenan API

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Also known as: 9000-07-1, Zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate, Carrageenan, native, Miv-150/za/cg, Miv-150/zinc acetate carrageenan, Zinc 1-(5-cyano-2-pyridyl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoyl-phenyl)cyclopropyl]urea diacetate

Molecular Formula

C₂₃H₂₃FN₄O₇Zn

Molecular Weight

551.8 g/mol

InChI Key

UHVMMEOXYDMDKI-JKYCWFKZSA-L

A water-soluble extractive mixture of sulfated polysaccharides from RED ALGAE. Chief sources are the Irish moss CHONDRUS CRISPUS (Carrageen), and Gigartina stellata. It is used as a stabilizer, for suspending COCOA in chocolate manufacture, and to clarify BEVERAGES.

1 2D Structure

Carrageenan API

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

zinc;1-(5-cyanopyridin-2-yl)-3-[(1S,2S)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate

2.1.2 InChI

InChI=1S/C19H17FN4O3.2C2H4O2.Zn/c1-2-15(25)11-4-5-13(20)17(18(11)26)12-7-14(12)23-19(27)24-16-6-3-10(8-21)9-22-16;2*1-2(3)4;/h3-6,9,12,14,26H,2,7H2,1H3,(H2,22,23,24,27);2*1H3,(H,3,4);/q;;;+2/p-2/t12-,14+;;;/m1.../s1

2.1.3 InChI Key

UHVMMEOXYDMDKI-JKYCWFKZSA-L

2.1.4 Canonical SMILES

CCC(=O)C1=C(C(=C(C=C1)F)C2CC2NC(=O)NC3=NC=C(C=C3)C#N)O.CC(=O)[O-].CC(=O)[O-].[Zn+2]

2.1.5 Isomeric SMILES

CCC(=O)C1=C(C(=C(C=C1)F)[C@@H]2C[C@@H]2NC(=O)NC3=NC=C(C=C3)C#N)O.CC(=O)[O-].CC(=O)[O-].[Zn+2]

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Carrageenin

2. Iota Carrageenan

3. Iota-carrageenan

4. Kappa Carrageenan

5. Kappa-carrageenan

6. Lambda Carrageenan

7. Lambda-carrageenan

2.2.2 Depositor-Supplied Synonyms

1. 9000-07-1

2. Zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate

3. Carrageenan, Native

4. Miv-150/za/cg

5. Miv-150/zinc Acetate Carrageenan

6. Zinc 1-(5-cyano-2-pyridyl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoyl-phenyl)cyclopropyl]urea Diacetate

2.2.3 Other Synonyms

1. Kappa-carrageenan

2. Carrageenan Api

2.3 Create Date

2013-07-09

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₃FN₄O₇Zn
Molecular Weight	551.8 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	5
Exact Mass	550.084219 g/mol
Monoisotopic Mass	550.084219 g/mol
Topological Polar Surface Area	195 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	647
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	4

4 Drug and Medication Information

4.1 Therapeutic Uses

Traditional Medicine: ... Used in tuberculosis, coughs, bronchitis, and intestinal problems, usually in the form of a decoction of the seaweed.

Leung, A.Y., Foster, S. Encyclopedia of Common Natural Ingredients Used in Food, Drugs, and Cosmetics. New York, NY. John Wiley & Sons, Inc. 1996., p. 126

Carrageenan, both in the degraded (molecular weight greater than or equal to 20,000) and undegraded forms, has been reported to alleviate peptic and duodenal ulcers in humans.

Leung, A.Y., Foster, S. Encyclopedia of Common Natural Ingredients Used in Food, Drugs, and Cosmetics. New York, NY. John Wiley & Sons, Inc. 1996., p. 125

5 Pharmacology and Biochemistry

5.1 Absorption, Distribution and Excretion

IN GUINEA-PIGS, NATIVE FORM OF CARRAGEENAN WAS NOT ABSORBED; DEGRADED CARRAGEENAN COULD NOT BE DETECTED IN URINE OF ANIMALS @ LEVELS OF ABOUT 0.3 MG/ML AFTER 1.85 G HAD BEEN ADMIN IN DRINKING-WATER OR @ LEVELS OF BETWEEN 0.03-0.3 MG/ML WHEN 4-15 MG/KG BODY WT OF DEGRADED CARRAGEENAN HAD BEEN ADMIN IV.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V10 186 (1976)

NATIVE CARRAGEENAN FED TO YOUNG RATS @ LEVELS OF 2-20% IN DIET WAS FOUND TO BE EXCRETED QUANTITATIVELY IN FECES.

NO STORAGE OF CARRAGEENAN WAS FOUND IN RHESUS MONKEYS GIVEN 1% NATIVE CARRAGEENAN IN DRINKING-WATER OVER 7-11 WEEKS, FOLLOWED BY 24-WK RECOVERY PERIOD. IN CONTRAST, DEGRADED CARRAGEENAN, WHICH WAS RETAINED AFTER ABSORPTION IN RETICULOENDOTHELIAL TISSUE, COULD STILL BE FOUND IN KUPFFER CELLS 6 MONTHS AFTER ADMIN.

5.2 Metabolism/Metabolites

Carrageen has inhibitory effects on pepsin activity in vitro. Its degraded form (no viscosity) and forms with low and high viscosities all exhibit antiproteolytic activities in vitro against papain.

Leung, A.Y., Foster, S. Encyclopedia of Common Natural Ingredients Used in Food, Drugs, and Cosmetics. New York, NY. John Wiley & Sons, Inc. 1996., p. 125

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