Disodium guanylate: Difference between revisions

Disodium guanylate
Names
	IUPAC name Disodium 5′-guanylate
	Systematic IUPAC name Disodium [(2R,3S,4R,5R)-5-(2-amino-4-oxo-2,3-dihydro-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
	Other names Sodium 5'-guanylate;
Identifiers
CAS Number	5550-12-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:132932 ;
ChemSpider	20407 ;
ECHA InfoCard	100.024.468
E number	E627 (flavour enhancer)
PubChem CID	21712;
UNII	B768T44Q8V ;
CompTox Dashboard (EPA)	DTXSID9044245 ;
	SMILES C1=NC2=C(N1C3C(C(C(O3)COP(=O)([O-])[O-])O)O)NC(=NC2=O)N.[Na+].[Na+];
Properties
Chemical formula	C10H12N5Na2O8P
Molar mass	407.186 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Latest revision as of 17:46, 11 September 2024

Disodium guanylate, also known as sodium 5'-guanylate and disodium 5'-guanylate, is a natural sodium salt of the flavor enhancing nucleotide guanosine monophosphate (GMP). Disodium guanylate is a food additive with the E number E627.^[2] It is commonly used in conjunction with glutamic acid.

As it is a fairly expensive additive, it is usually not used independently of glutamic acid; if disodium guanylate is present in a list of ingredients but MSG does not appear to be, it is likely that glutamic acid is provided as part of another ingredient such as a processed soy protein complex. It is often added to foods in conjunction with disodium inosinate; the combination is known as disodium 5'-ribonucleotides.

Disodium guanylate is produced by fermentation.^[3]^[4] It is often added to instant noodles, potato chips and other snacks, savory rice, tinned vegetables, cured meats, and packaged soup.

References

^ "SID 164216535 - PubChem". pubchem.ncbi.nlm.nih.gov.
^ E627 : Sodium guanylate
^ Conn, Helen (1 February 1992). ""Umami": The Fifth Basic Taste". Nutrition & Food Science. 92 (2): 21–23. doi:10.1108/EUM0000000000953.
^ Kinoshita, Kazumoto; Shiro, Teruo; Yamazaki, Akihiro; Kumashiro, Izumi; Takenishi, Tadao; Tsunoda, Toshinao (July 1967). "Industrial production of disodium 5?-guanylate". Biotechnology and Bioengineering. 9 (3): 329–342. doi:10.1002/bit.260090306. S2CID 84216811.

[1] "SID 164216535 - PubChem". pubchem.ncbi.nlm.nih.gov.

[fin-2] E627 : Sodium guanylate

[3] Conn, Helen (1 February 1992). ""Umami": The Fifth Basic Taste". Nutrition & Food Science. 92 (2): 21–23. doi:10.1108/EUM0000000000953.

[4] Kinoshita, Kazumoto; Shiro, Teruo; Yamazaki, Akihiro; Kumashiro, Izumi; Takenishi, Tadao; Tsunoda, Toshinao (July 1967). "Industrial production of disodium 5?-guanylate". Biotechnology and Bioengineering. 9 (3): 329–342. doi:10.1002/bit.260090306. S2CID 84216811.

[1]

[2]

[3]

[4]

@@ Line 10: / Line 10: @@
 | ImageSize1=240
 | ImageAlt1 = Ball-and-stick model of the component ions of disodium guanylate
+| IUPACName = Disodium 5′-guanylate
-| IUPACName=disodium [(2''R'',3''S'',4''R'',5''R'')-5-(2-amino-6-oxo-3''H''-purin-9-yl)-3,4-dihydroxy-2-tetrahydrofuranyl]methyl phosphate {{Citation needed|date=April 2010}}
+| SystematicName = Disodium [(2''R'',3''S'',4''R'',5''R'')-5-(2-amino-4-oxo-2,3-dihydro-9''H''-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
-| OtherNames=sodium 5'-guanylate<br>disodium 5'-guanylate
+| OtherNames = {{Unbulleted list|Sodium 5'-guanylate}}
 |Section1={{Chembox Identifiers
-| CASNo_Ref = {{cascite|correct|??}}<ref>http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=164216535&loc=es_rss</ref>
+| CASNo_Ref = {{cascite|correct|??}}<ref>{{cite web |url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=164216535&loc=es_rss |title=SID 164216535 - PubChem |website=pubchem.ncbi.nlm.nih.gov}}</ref>
 | CASNo=5550-12-9
 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
 | ChemSpiderID = 20407
 | PubChem=21712
+| ChEBI_Ref = {{ebicite|changed|EBI}}
+| ChEBI = 132932
 | UNII_Ref = {{fdacite|changed|FDA}}
 | UNII = B768T44Q8V
@@ Line 37: / Line 40: @@
 }}
-'''Disodium guanylate''', also known as '''sodium 5'-guanylate''' and '''disodium 5'-guanylate''', is a natural [[sodium]] [[salt (chemistry)|salt]] of the [[flavor enhancer|flavor enhancing]] nucleotide [[guanosine monophosphate]] (GMP). Disodium guanylate is a [[food additive]] with the [[E number]] E627.<ref name=fin>[http://www.food-info.net/uk/e/e627.htm E627 : Sodium guanylate]</ref> It is commonly used in conjunction with [[glutamic acid]] ([[monosodium glutamate]], MSG).
+'''Disodium guanylate''', also known as '''sodium 5'-guanylate''' and '''disodium 5'-guanylate''', is a natural [[sodium]] [[salt (chemistry)|salt]] of the [[flavor enhancer|flavor enhancing]] nucleotide [[guanosine monophosphate]] (GMP). Disodium guanylate is a [[food additive]] with the [[E number]] E627.<ref name=fin>[http://www.food-info.net/uk/e/e627.htm E627 : Sodium guanylate]</ref> It is commonly used in conjunction with [[glutamic acid]].
-As it is a fairly expensive additive, it is not used independently of glutamic acid; if disodium guanylate is present in a list of ingredients but MSG does not appear to be, it is likely that glutamic acid is provided as part of another ingredient such as a processed [[soy protein]] [[protein complex|complex]]. It is often added to foods in conjunction with [[disodium inosinate]]; the combination is known as [[disodium 5'-ribonucleotides]].
+As it is a fairly expensive additive, it is usually not used independently of [[glutamic acid]]; if disodium guanylate is present in a list of ingredients but MSG does not appear to be, it is likely that glutamic acid is provided as part of another ingredient such as a processed [[soy protein]] [[protein complex|complex]]. It is often added to foods in conjunction with [[disodium inosinate]]; the combination is known as [[Disodium ribonucleotides|disodium 5'-ribonucleotides]].
-Disodium guanylate is produced from dried seaweed and is often added to [[instant noodles]], [[potato chips]] and other [[snack]]s, savory [[rice]], tinned [[vegetables]], cured [[meat]]s, and packaged [[soup]].
+Disodium guanylate is produced by fermentation.<ref>{{cite journal |last1=Conn |first1=Helen |title="Umami": The Fifth Basic Taste |journal=Nutrition & Food Science |date=1 February 1992 |volume=92 |issue=2 |pages=21–23 |doi=10.1108/EUM0000000000953}}</ref><ref>{{cite journal |last1=Kinoshita |first1=Kazumoto |last2=Shiro |first2=Teruo |last3=Yamazaki |first3=Akihiro |last4=Kumashiro |first4=Izumi |last5=Takenishi |first5=Tadao |last6=Tsunoda |first6=Toshinao |title=Industrial production of disodium 5?-guanylate |journal=Biotechnology and Bioengineering |date=July 1967 |volume=9 |issue=3 |pages=329–342 |doi=10.1002/bit.260090306|s2cid=84216811 }}</ref> It is often added to [[instant noodles]], [[potato chip]]s and other [[snack]]s, savory [[rice]], tinned [[vegetables]], cured [[meat]]s, and packaged [[soup]].
-==Nutritional information==
-Disodium guanylate is not safe for babies under twelve weeks, and should generally be avoided by [[Asthma|asthmatics]] and people with [[gout]], as guanylates are metabolized to [[Purine metabolism#Disorders|purines]]. However, the typical amounts found in food are generally too low to produce significant side effects.<ref name=fin/>  Since it is often produced from fish,<ref name=fin/> [[vegan]]s and [[vegetarian]]s may wish to avoid it unless the product is specifically labeled as vegan or vegetarian. Such labels require the use of non-animal derived sources, such as seaweed or [[yeast]].
 ==See also==
+{{Columns-list|colwidth=16em|
 * [[Acceptable daily intake]]
+* [[Glutamate flavoring]]
+* [[Kikunae Ikeda]]
+* [[Umami]]
+* [[Ajinomoto]]
+* [[Tien Chu Ve-Tsin]]
+* [[Glutamic acid]]
+* [[Disodium glutamate]]
+* [[Monopotassium glutamate]]
 * [[Disodium inosinate]]
+* [[Inosinic acid]]
+* [[Guanosine monophosphate]]
+* [[Adenosine monophosphate]]
+* [[Hypoxanthine-guanine phosphoribosyltransferase]]
+* [[Ribonucleoside]]
+}}
 ==References==
@@ Line 55: / Line 69: @@
 {{DEFAULTSORT:Disodium Guanylate}}
-[[Category:Sodium compounds]]
+[[Category:Organic sodium salts]]
 [[Category:Nucleotides]]
 [[Category:Flavor enhancers]]
+[[Category:E-number additives]]