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Calcium Levulinate

HCID 68651
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Grundinformationen

CAS
5743-49-7
Standard-SMILES
CC(=O)CCC(=O)[O-].CC(=O)CCC(=O)[O-].O.O.[Ca+2]
InChIKey
WQFDRFDIWAMOPA-UHFFFAOYSA-L
Summenformel
C10H18CaO8
Durchschnittliche Molmasse
306,32 g/mol
Monoisotopische Masse
306,06275852

Überblick

The relatively new calcium levulinate is produced from a direct reaction between L- or levulinic acid levulose and calcium hydroxide. The resultant calcium levulinate formulation, when used as a calcium supplement, possesses a high calcium content that is observed to be 14.8% higher than the content typically found in calcium lactate. This formulation is considered a low molecular weight organic calcium ion type that is easily absorbed through the intestinal wall. This new application of calcium is intended for use as a food fortifier, to fortify foods like sauces, condiments, beer, beverages, soft drinks, milk and milk products, soy milk and soy products with calcium nutrition. Calcium levulinate can be used alone, or with calcium lactate, calcium chloride, and other compounds, either for pharmaceutical tablets, capsules, or injections preparation.

Namen und Bezeichner

Bevorzugter Name
Calcium Levulinate
IUPAC
calcium;bis(4-oxopentanoate);dihydrate
Englischer Name
Calcium levulinate dihydrate
Summenformel
C10H18CaO8
Molmasse
306.32

Namen und Synonyme

Calcium levulinate dihydrate5743-49-7DTXSID8046539T6133SO781DTXCID6026539RefChem:1080692Calcium Levulinatecalcium;4-oxopentanoate;dihydrateCalcium levulinate (1:2) dihydratePentanoic acid, 4-oxo-,calcium salt, hydrate (2:1:2)Pentanoic acid, 4-oxo-, calcium salt (2:1), dihydrateCAS-5743-49-7
Weitere Namen anzeigen
Fructose Calciumcalcii laevulinaslevulinic acid hemicalciumCalcium levulinate 2-hydrateFructonate calcium dihydrateCalcium Levulinate (1 g) (AS)γ-Ketovaleric acid calcium saltcalcium 4-ketovalerate dihydrate
NCGC00166102-01UNII-T6133SO781calcium 4-oxopentanoate dihydrateCalcium levulinate [USP:INN:BAN]Calcium levulinate (USP)SCHEMBL377115Calcium levulinate dihydrate CRSCHEMBL3186421

Datenbank-Bezeichner

CAS
5743-49-7、591-64-0

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
116 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
8
Frei drehbare Bindungen
4
Schwere Atome
19
Formalladung
0
Komplexität
101

Experimentelle und physikochemische Eigenschaften

Chemical ClassesMetals -> Organic Acids, Metal Salts
Physical DescriptionDihydrate: Solid; [Merck Index] Solid; [TCI America MSDS]

Physikochemische Eigenschaften

Schmelzpunkt
121 to · 121.0 to 125.0 °C
storage temp.
Store at room temperature
Löslichkeit
Freely soluble in water, very slightly soluble in ethanol (96 per cent), practically insoluble in methylene chloride.
Merck
14 · 14,1679
BRN
3764203 · 3764203
Major Application
pharmaceutical (small molecule)
InChI
InChI=1S/2C5H8O3.Ca/c2*1-4(6)2-3-5(7)8;/h2*2-3H2,1H3,(H,7,8);/q;;+2/p-2
InChIKey
APKDPOQXVKRLEP-UHFFFAOYSA-L
SMILES
C(=O)(O[Ca]OC(=O)CCC(=O)C)CCC(=O)C
LogP
-0.49 · -0.490 (est)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Chemical: Pentanoic acid, 4-oxo-, calcium salt, trihydrate

Calcium Levulinate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Hazards SummaryMay cause irritation; [TCI America MSDS] See Calcium.

Sicherheitsdaten

wgk
3
hs_code
2918300000
RTECS-Nr.
SA4000000
Speicherklasse
11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

Protein Binding · 1 Eintrag

Readily accessible data regarding the protein binding of calcium levulinate is not available, although many different calcium-binding proteins exist, with different cellular and tissue distribution and involvement in specific biological function. Some of these proteins include calmodulin, calsequestrin, calretinin, and calcineurin, among others.

Pharmacodynamics · 1 Eintrag

The relatively new calcium levulinate is produced from a direct reaction between L- or levulinic acid levulose and calcium hydroxide. The resultant calcium levulinate formulation, when used as a calcium supplement, possesses a high calcium content that is observed to be 14.8% higher than the content typically found in calcium lactate. Moreover, this formulation also demonstrates a high solubility of more than 30% at 25℃. Furthermore, the calcium levulinate is believed to be non-toxic and non-allergic, making it especially suitable for injection or infusion administrations. Additionally, this levulinate formulation is reported as having a good taste, little irritation with a pH value of 7, and good stability such that no precipitation or deterioration occurs during use. Finally, this calcium levulinate formulation is also believed to have good compatibility with calcium lactate, calcium chloride, and other material complexes which allows the formulation to also complex effectively with a diverse variety of foodstuffs and pharmaceutical dosage forms.

Mechanism of Action · 1 Eintrag

Much like most calcium supplements, once calcium levulinate dissociates in the body after administration, absorption of the supplemental calcium ions across the intestinal wall serves to enhance calcium stores in the body. Regardless, levulinic acid (LA) is a commonly used chemical with one carbonyl group, one carboxyl group, and alpha-H comprised in its inner structure, which belongs to short-chain and non-volatile fatty acids. Moreover, the carbon-oxygen double bond from LA's carbonyl group possesses a strong polarity, where the oxygen atom has a stronger electron attracting ability compared to the carbon atom, such that the pi electron will ultimately transfer into the greater electronegative oxygen, therefore resulting in the formation of a positive charge center in the carbon atom. The electrophilic center of the carbon atom subsequently plays a critical role when the carbonyl group performs chemical reactions. Owing to the relatively strong electron receptor effect of the oxygen atom of the carbonyl group, LA has higher dissociation constants than a common saturated acid, which allows it to possess a stronger corresponding acidity. Furthermore, LA can be isomerized into the enol-isomer, owing to the presence of the carbonyl group. The chemical structure of LA consequently has several highly active sites, which facilitates it being used as a chemical platform for preparing many other chemical products. For example, the special structure of LA allows various kinds of products to be generated by way of esterification, halogenation, hydrogenation, oxy-dehydrogenation, and/or condensation, among many other methods.

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
PubChem CID
68651
DTXSID
DTXSID8046539
ChEMBL
CHEMBL2106516、CHEMBL3186421
UNII
T6133SO781
Biological Half-LifeReadily accessible data regarding the half-life of calcium levulinate is not available.
Metabolism/Metabolites · 1 Eintrag

Although calcium levulinate dissociates into absorbable calcium ion once it is administered into the body, there have been studies to suggest that the levulinate component is metabolized to 4-hydroxypentanoate - a compound that has similar pharmacologic effects as but at a lower level of potency than the 'date rape' drug gamma-hydroxybutyrate.

Absorption, Distribution and Excretion · 4 Einträge

General calcium absorption occurs primarily in the duodenum by an active transcellular and saturable system, which is stimulated and regulated by 1,25(OH)2D,25 and through a passive and vitamin D-independent paracellular transport in the jejunum and ileum, and even in the colon - where absorption is only about 4% even when the intake is high. Ultimately, calcium absorption depends mainly on the amount of intake - in general, absorption increases at lower intakes and decreases at high intakes. Readily accessible data regarding the specific absorption of calcium levulinate is not available although the formulation is considered a low molecular weight organic calcium ion type that is easily absorbed through the intestinal wall.

Calcium leaves the body mainly in urine and feces, but also in other body tissues and fluids, like sweat. Overall, a typical daily calcium loss for a healthy adult man or woman via renal excretion is approximately 5 mmol/day while endogenous fecal calcium losses are about 2.1 mg/kg per day in adults and about 1.4 mg/kg per day in children.

99% of the body's calcium supply is stored in the bones and teeth where it supports their structure and function. Elsewhere, 1% or less of this calcium supply is used for essential metabolic functions like vascular contraction and vasodilation, muscle function, nerve transmission, intracellular signaling, and hormonal secretion, among other activities.

Despite inter-individual differences, general clinical lab tests list some reference calcium clearance values as being considered a 'normal range', like urine calcium as approximately < 250 mg/24 h.

Verwendung und Herstellung

UsesUsed as a calcium supplement; May be used in veterinary medicine in hypocalcemic states; [Merck Index]

Anwendungen

VerwendenReplenisher (calcium).

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Ergänzende Hinweise

DefinitionChEBI: Calcium levulinate anhydrous is an organic molecular entity.