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Calcium Levulinate

HCID 68651
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Basic information

CAS
5743-49-7
Standard SMILES
CC(=O)CCC(=O)[O-].CC(=O)CCC(=O)[O-].O.O.[Ca+2]
InChIKey
WQFDRFDIWAMOPA-UHFFFAOYSA-L
Molecular formula
C10H18CaO8
Average molar mass
306.32 g/mol
Monoisotopic mass
306.06275852

Overview

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.

Names & identifiers

Preferred name
Calcium Levulinate
IUPAC
calcium;bis(4-oxopentanoate);dihydrate
English name
Calcium levulinate dihydrate
Molecular formula
C10H18CaO8
Molecular weight
306.32

Names & synonyms

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
Show more names
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

Properties

Computed structural properties

Topological polar surface area
116 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
8
Rotatable bonds
4
Heavy atoms
19
Formal charge
0
Complexity
101

Experimental & physicochemical properties

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

Physicochemical properties

Melting point
121 to · 121.0 to 125.0 °C
storage temp.
Store at room temperature
solubility
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)
FDA UNII
6133 SO781 · T6133SO781

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Regulatory Information · 2 items

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.

Safety data

wgk
3
rtecs
SA4000000
hs_code
2918300000
Storage Class
11 - Combustible Solids

Chemistry & industry

Pharmacology

Protein Binding · 1 item

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 item

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 item

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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Compound notes

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Database identifiers

CAS
5743-49-7、591-64-0
PubChem CID
68651
DTXSID
DTXSID8046539
ChEMBL
CHEMBL2106516、CHEMBL3186421
UNII
T6133SO781
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
WGK Germany
3 · 3
RTECS
4000000 · SA4000000
HS Code
2918300000 · 2918300000
Storage Class
11 · 11 - Combustible Solids
Biological Half-LifeReadily accessible data regarding the half-life of calcium levulinate is not available.
Metabolism/Metabolites · 1 item

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 items

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.

Uses & manufacturing

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

Applications

UsesCalcium Levulinate is a salt of Levulinic Acid (L379500), derived from the degredation of cellulose and is a potential precursor to biofuels. Levulinic acid is also a photosensitizer for photodynamic therapy.

UsesReplenisher (calcium).

Additional notes

DefinitionChEBI: Calcium levulinate anhydrous is an organic molecular entity.