Calcium diglutamate: Difference between revisions
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| ImageFile = Calcium diglutamate.svg |
| ImageFile = Calcium diglutamate.svg |
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| IUPACName = Calcium bis[(2''S'')- 2-amino-4-carboxy-butyrate] |
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| ImageSize = |
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| IUPACName = Calcium dihydrogen (2''S'')-2-aminopentanedioate<!-- unverified and seems incorrect --> |
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| index_label = anhydrous |
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| index1_label = tetrahydrate |
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| ChemSpiderID = 2766261 |
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| InChIKey = ZKUDDWCZGPUNQH-VDEFSOALBX |
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| CASNo = 5996-22-5 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo1 = 69704-19-4 |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 9FA5OTO85L |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = IPW75840KB |
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| EINECS = |
| EINECS = |
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| PubChem = |
| PubChem = 3527266 |
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| PubChem1 = 71310219 |
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| SMILES = C(CC(=O)O) |
| SMILES = C(CC(=O)[O-])C(C(=O)[O-])N.C(CC(=O)[O-])C(C(=O)[O-])N.[Ca+2] |
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| InChI = |
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| InChI = 1/2C5H9NO4.Ca.2H/c2*6-3(5(9)10)1-2-4(7)8;;;/h2*3H,1-2,6H2,(H,7,8)(H,9,10);;;/p-4/t2*3-;;;/m00.../s1/r2C5H9NO4.CaH2/c2*6-3(5(9)10)1-2-4(7)8;/h2*3H,1-2,6H2,(H,7,8)(H,9,10);1H2/p-4/t2*3-;/m00./s1 |
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| Beilstein = 11158966 |
| Beilstein = 11158966 |
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| Ca=1 | C=10 | H=16 | N=2 | O=8 |
| Ca=1 | C=10 | H=16 | N=2 | O=8 |
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| Appearance = |
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| pKa = |
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| pKb = }} |
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'''Calcium diglutamate''', sometimes abbreviated '''CDG''' and also called '''calcium |
'''Calcium diglutamate''', sometimes abbreviated '''CDG''' and also called '''calcium biglutamate''', is a [[Compound (chemistry)|compound]] with formula Ca(C<sub>5</sub>H<sub>8</sub>NO<sub>4</sub>)<sub>2</sub>. It is a [[calcium]] [[acid salt]] of [[glutamic acid]]. CDG is a [[flavor enhancer]] ([[E number]] E623)—it is the calcium analog of [[monosodium glutamate]] (MSG). Because the [[Glutamic acid (flavor)|glutamate is the actual flavor-enhancer]], CDG has the same flavor-enhancing properties as MSG but without the increased sodium content.<ref>{{Cite journal| first1 = P.| last2 = Woodward | first2 = D. | first3 = T.| last4 = Shoobridge| last3 = Beard | first4 = A. | first5 = M.| title = Calcium diglutamate improves taste characteristics of lower-salt soup| type = Free full text| last1 = Ball| last5 = Ferrier| journal = European Journal of Clinical Nutrition| volume = 56| issue = 6| pages = 519–523| date=Jun 2002 | issn = 0954-3007| pmid = 12032651| doi = 10.1038/sj.ejcn.1601343| doi-access = }}</ref> Notably, only the <small>L</small> isomer is used in flavouring as <small>D</small>-glutamate does not have an umami/savoury flavour.<ref name="Gustatory_D-amino_Misako">{{cite journal | last1=Kawai | first1=Misako | last2=Sekine-Hayakawa | first2=Yuki | last3=Okiyama | first3=Atsushi | last4=Ninomiya | first4=Yuzo | title=Gustatory sensation of <small>L</small>- and <small>D</small>-amino acids in humans | journal=Amino Acids | volume=43 | issue=6 | date=2012 | issn=0939-4451 | doi=10.1007/s00726-012-1315-x | pages=2349–2358| pmid=22588481 }}</ref><ref name="TasteQualities_D-amino">{{cite journal | last1=Schiffman | first1=S | last2=Sennewald | first2=K | last3=Gagnon | first3=J | title=Comparison of taste qualities and thresholds of <small>D</small>- and <small>L</small>-amino acids | journal=Physiology & Behavior | volume=27 | issue=1 | date=1981 | doi=10.1016/0031-9384(81)90298-5 | pages=51–59| pmid=7267802 }}</ref> |
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As a soluble source of calcium ions, this chemical is also used as a [[first-aid]] treatment for exposure to [[hydrofluoric acid]].<ref>{{cite web |url= http://www.ee.byu.edu/cleanroom/first_aid.phtml |title= First Aid for Chemical and Cleanroom Laboratories |accessdate= 2009-06-10 |archive-date= 2009-04-30 |archive-url= https://web.archive.org/web/20090430024822/http://www.ee.byu.edu/cleanroom/first_aid.phtml |url-status= dead }}<!-- also mentioned in various MSDS for HF and other ionic F- salts--></ref> |
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==Synthesis and reactions== |
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Calcium di-glutamate can be prepared by reacting [[calcium carbonate]] with two molar equivalents of [[glutamic acid]]:<ref name="AlkalineEarthSaltsGlutamic">{{cite journal | last1=Sakata | first1=Yoshiki | last2=Horikawa | first2=Toshiyuki | last3=Takenouchi | first3=Kuniharu | title=Alkaline Earth Salts of Glutamic Acid and Optical Resolution of their Racemic Modifications | journal=Agricultural and Biological Chemistry | volume=27 | issue=7 | date=1963 | issn=0002-1369 | doi=10.1080/00021369.1963.10858140 | pages=518–525}}</ref> |
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:CaCO<sub>3</sub> + 2 HOOC(CH<sub>2</sub>)<sub>2</sub>CH(NH<sub>2</sub>)COOH → Ca(OOC(CH<sub>2</sub>)<sub>2</sub>CH(NH<sub>3</sub>)COO)<sub>2</sub> + H<sub>2</sub>O + CO<sub>2</sub>↑ |
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Concentration of the solution to a syrup under reduced pressure, followed by gradual crystallisation, affords the monohydrate.<ref name="AlkalineEarthSaltsGlutamic"/> Structurally, the glutamate anion is zwitterionic, with the amino group protonated (p''K''<sub>a</sub> = 9.47) and both carboxylic-acid groups (p''K''<sub>a</sub> = 2.10, 4.07) in their deprotonated carboxylate form.<ref name="CBG.4H2O_CrystalStructure">{{cite journal | last1=Einspahr | first1=H. | last2=Bugg | first2=C. E. | title=Calcium binding to α-amino acids: the crystal structure of calcium di-<small>L</small>-glutamate tetrahydrate | journal=Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry | volume=35 | issue=2 | date=1979-02-15 | doi=10.1107/S0567740879003435 | pages=316–321}}</ref> |
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Calcium di-<small>L</small>-glutamate can be used to prepare other glutamates through metathesis with a soluble sulfate, carbonate or hydroxide salt. For example, manganese(II) di-<small>L</small>-glutamate can be prepared through metathesis with [[manganese(II) sulphate]]:<ref name="Mn_AminoAcidComplexes">{{cite journal | last1=Devereux | first1=Michael | last2=Jackman | first2=Maura | last3=McCann | first3=Malachy | last4=Casey | first4=Michael | title=Preparation and catalase-type activity of manganese(II) amino acid complexes | journal=Polyhedron | volume=17 | issue=1 | date=1998 | doi=10.1016/S0277-5387(97)00211-8 | pages=153–158}}</ref> |
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:Ca(OOC(CH<sub>2</sub>)<sub>2</sub>CH(NH<sub>3</sub>)COO)<sub>2</sub> + MnSO<sub>4</sub> → Mn(OOC(CH<sub>2</sub>)<sub>2</sub>CH(NH<sub>3</sub>)COO)<sub>2</sub> + CaSO<sub>4</sub>↓ |
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<!-- not to be confused with monocalcium glutamate (calcium (2''S'')-2-aminopentanedioate) the 1:1 salt Ca(C<sub>5</sub>H<sub>7</sub>NO<sub>4</sub>) CID24148 --> |
<!-- not to be confused with monocalcium glutamate (calcium (2''S'')-2-aminopentanedioate) the 1:1 salt Ca(C<sub>5</sub>H<sub>7</sub>NO<sub>4</sub>) CID24148 --> |
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<references/> |
<references/> |
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{{Calcium compounds}} |
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[[Category:Glutamates]] |
[[Category:Glutamates]] |
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[[Category:Calcium compounds]] |
[[Category:Calcium compounds]] |
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[[Category:E-number additives]] |
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{{organic-compound-stub}} |
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Latest revision as of 15:38, 11 September 2024
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| Names | |
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| IUPAC name
Calcium bis[(2S)- 2-amino-4-carboxy-butyrate]
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Other names
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| Identifiers | |
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3D model (JSmol)
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| Abbreviations | CDG, CBG |
| 11158966 | |
| ChemSpider |
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| ECHA InfoCard | 100.025.307 |
| E number | E623 (flavour enhancer) |
PubChem CID
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| UNII |
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CompTox Dashboard (EPA)
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| Properties | |
| C10H16CaN2O8 | |
| Molar mass | 332.322 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Calcium diglutamate, sometimes abbreviated CDG and also called calcium biglutamate, is a compound with formula Ca(C5H8NO4)2. It is a calcium acid salt of glutamic acid. CDG is a flavor enhancer (E number E623)—it is the calcium analog of monosodium glutamate (MSG). Because the glutamate is the actual flavor-enhancer, CDG has the same flavor-enhancing properties as MSG but without the increased sodium content.[1] Notably, only the L isomer is used in flavouring as D-glutamate does not have an umami/savoury flavour.[2][3]
As a soluble source of calcium ions, this chemical is also used as a first-aid treatment for exposure to hydrofluoric acid.[4]
Synthesis and reactions
[edit]Calcium di-glutamate can be prepared by reacting calcium carbonate with two molar equivalents of glutamic acid:[5]
- CaCO3 + 2 HOOC(CH2)2CH(NH2)COOH → Ca(OOC(CH2)2CH(NH3)COO)2 + H2O + CO2↑
Concentration of the solution to a syrup under reduced pressure, followed by gradual crystallisation, affords the monohydrate.[5] Structurally, the glutamate anion is zwitterionic, with the amino group protonated (pKa = 9.47) and both carboxylic-acid groups (pKa = 2.10, 4.07) in their deprotonated carboxylate form.[6]
Calcium di-L-glutamate can be used to prepare other glutamates through metathesis with a soluble sulfate, carbonate or hydroxide salt. For example, manganese(II) di-L-glutamate can be prepared through metathesis with manganese(II) sulphate:[7]
- Ca(OOC(CH2)2CH(NH3)COO)2 + MnSO4 → Mn(OOC(CH2)2CH(NH3)COO)2 + CaSO4↓
References
[edit]- ^ Ball, P.; Woodward, D.; Beard, T.; Shoobridge, A.; Ferrier, M. (Jun 2002). "Calcium diglutamate improves taste characteristics of lower-salt soup". European Journal of Clinical Nutrition (Free full text). 56 (6): 519–523. doi:10.1038/sj.ejcn.1601343. ISSN 0954-3007. PMID 12032651.
- ^ Kawai, Misako; Sekine-Hayakawa, Yuki; Okiyama, Atsushi; Ninomiya, Yuzo (2012). "Gustatory sensation of L- and D-amino acids in humans". Amino Acids. 43 (6): 2349–2358. doi:10.1007/s00726-012-1315-x. ISSN 0939-4451. PMID 22588481.
- ^ Schiffman, S; Sennewald, K; Gagnon, J (1981). "Comparison of taste qualities and thresholds of D- and L-amino acids". Physiology & Behavior. 27 (1): 51–59. doi:10.1016/0031-9384(81)90298-5. PMID 7267802.
- ^ "First Aid for Chemical and Cleanroom Laboratories". Archived from the original on 2009-04-30. Retrieved 2009-06-10.
- ^ a b Sakata, Yoshiki; Horikawa, Toshiyuki; Takenouchi, Kuniharu (1963). "Alkaline Earth Salts of Glutamic Acid and Optical Resolution of their Racemic Modifications". Agricultural and Biological Chemistry. 27 (7): 518–525. doi:10.1080/00021369.1963.10858140. ISSN 0002-1369.
- ^ Einspahr, H.; Bugg, C. E. (1979-02-15). "Calcium binding to α-amino acids: the crystal structure of calcium di-L-glutamate tetrahydrate". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 35 (2): 316–321. doi:10.1107/S0567740879003435.
- ^ Devereux, Michael; Jackman, Maura; McCann, Malachy; Casey, Michael (1998). "Preparation and catalase-type activity of manganese(II) amino acid complexes". Polyhedron. 17 (1): 153–158. doi:10.1016/S0277-5387(97)00211-8.