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GUANYLIC ACID

Guanylic acid serves as an important nucleotide in biochemical and molecular biology research.
Guanylic acid is used in studies involving nucleic acid metabolism, cellular signaling, and genetic processes.
Guanylic acid functions as a precursor and intermediate in the synthesis of various nucleotide-based compounds.

CAS Number: 85-32-5
EC Number: 201-602-6
Molecular Formula: C10H14N5O8P
Molecular Weight: 363.22 g/mol

SYNONYMS:
5′-Guanylic acid, [(2R,3S,4R,5R)-5-(2-Amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate, 5′-Guanidylic acid, E number E626, Guanylic Acid, Guanosine Monophosphate, GMP, 5'-Guanylic Acid, 5'-GMP, Guanosine 5'-Monophosphate, Guanosinic Acid, Guanosine Monophosphoric Acid, Guanine Ribonucleotide, 5'-Guanosine Monophosphate, Guanylate, Guanosine-5'-Phosphate, Guanosine Phosphate, Guanylic Acid Free Acid, [(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate, guanilic acid, guanosine 5'-monophosphate, guanosine 5'-monophosphoric acid, 5'-guanylic acid, 5'-Guanylic acid, 85-32-5, guanosine-5'-monophosphate, guanosine monophosphate, Guanidine monophosphate, Guanosine 5'-monophosphoric acid, Guanosine 5' Monophosphate, DTXSID9044295, E 626, INS NO.626, 16597955EP, INS-626, [(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate, E-626, {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid, Acid, Guanylic, 5' Guanylic Acid, Acid, 5'-Guanylic, Monophosphate, Guanosine, 5'-Monophosphate, Guanosine, (((2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl)methoxy)phosphonic acid, ((2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl)methyl dihydrogen phosphate, RefChem:389027, DTXCID7024295, 201-598-8, Guanosine 5'-monophosphate, guanylic acid, 5'-Gmp, Guanosine 5'-phosphate, guanylate, guanosine-monophosphate, GMP, C10H14N5O8P, guanosine-phosphate, MFCD00057066, Guanosine 5'-phosphoric acid, CHEBI:17345, AI3-28539, CHEMBL283807, Guanosine 5'-(dihydrogen phosphate), 5GP, 5'-Guanylicacid, guanosine-5'-phosphate, Guanosine-5'-monophosphate disodium salt, EINECS 201-598-8, guanylsaure, 5'-GMP, 5'-guanosine monophosphate, 1sgx, 2fxv, UNII-16597955EP, Xylo-GMP, 1g9t, Guanosine 5'-phosphorate, Guanosine-5-Monophosphate, Epitope ID:190357, [3h]guanosine monophosphate, SCHEMBL5854, SCHEMBL94794, 128952-18-1, 5'-Guanylic acid (Standard), GTPL5123, 5'-GUANYLIC ACID [MI], HY-N5134R, 5'-Guanylic acid (8CI,9CI), MSK6903, 1w25, guanine riboside-5-phosphoric acid, HY-N5134, BDBM50010318, Guanosine-5'-(dihydrogen phosphate), AKOS025311571, AKOS040744252, DB01972, EBC-277067, NG09355, 29593-02-0, SY232082, CS-0032523, NS00015253, C00144, Q422473, Z2289798741, 38CABC90-82D3-4544-9566-34C06A477068, Guanosine-5'-monophosphate 1000 microg/mL in Acetonitrile:Water, ((2R,3S,4R,5R)-5-(2-Amino-6-oxo-1H-purin-9(6H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyldihydrogenphosphate, [(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate, [(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate, {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid, GUANYLIC ACID, GMP, GMP, Guanosine monophosphate, GMP, 5’-gmp, guanylate, GUANYLIC ACID, Guanidylic acid, [(2R,3S,4R,5R)-5-(2-Amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate, G-5′-P, GMP·H2, Guo-5'-P, GMP FREE

Guanylic acid is the monophosphoric ester of guanine, i.e., the nucleotide containing guanine, d-ribose, and phosphoric acid.
Guanylic acid may be esterified to either the 2, 3, or 5 carbon of ribose, yielding guanosine-2′-phosphate, guanosine-3′-phosphate, and guanosine-
Guanylic acid (5'-GMP) is an important nucleotide compound and a component of RNA.

Guanylic acid is involved in various metabolic pathways and exhibits certain biological activities, such as potential roles in regulating nutrient metabolism and enhancing immunity.
Guanylic acid is a purine ribonucleoside 5'-monophosphate having guanine as the nucleobase.

Guanylic acid has a role as a metabolite, a biomarker, a mouse metabolite and an Escherichia coli metabolite.
Guanylic acid is a purine ribonucleoside 5'-monophosphate and a guanosine 5'-phosphate.
Guanylic acid is a conjugate acid of a guanosine 5'-monophosphate(2-).

Guanylic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
Guanylic acid has been reported in Drosophila melanogaster, Bombyx mori, and other organisms with data available.
Guanylic acid is a metabolite found in or produced by Saccharomyces cerevisiae.

Guanylic acid is a guanine nucleotide containing one phosphate group esterified to the sugar moiety and found widely in nature.
Guanylic acid is known as E number reference E626.
In the form of Guanylic acid's salts, such as disodium guanylate (E627), dipotassium guanylate (E628) and calcium guanylate (E629), are food additives used as flavor enhancers to provide the umami taste.

Guanylic acid belongs to the family of purine nucleotides and occupies a central position in cellular biochemistry.
Guanylic acid functions as both a structural component of RNA and a precursor to numerous biologically active nucleotide derivatives.
Commercially, guanylic acid is often encountered in the form of its salts, particularly disodium guanylate, which is widely used as a food additive.

Together with inosinic acid and glutamates, guanylic acid forms one of the most effective flavor-enhancing systems used in modern food technology.
Its combination of biological importance, flavor-enhancing activity, and biochemical versatility makes guanylic acid a significant compound in food science, molecular biology, biotechnology, and pharmaceutical research.

Guanylic Acid, commonly known as Guanosine Monophosphate (GMP), is a naturally occurring nucleotide composed of the nucleobase guanine, the sugar ribose, and a phosphate group.
Guanylic acid is an important biological molecule found in all living cells and serves as a fundamental building block of ribonucleic acid (RNA).

Guanylic acid plays essential roles in cellular metabolism, nucleic acid synthesis, signal transduction, energy transfer, and biochemical regulation.
Guanosine monophosphate (GMP), also known as 5′-guanidylic acid or guanylic acid (conjugate base guanylate), is a nucleotide that is used as a monomer in RNA.
Guanylic acid is an ester of phosphoric acid with the nucleoside guanosine.

Guanylic acid consists of the phosphate group, the pentose sugar ribose, and the nucleobase guanine; hence it is a ribonucleotide monophosphate.
Guanylic acid is commercially produced by microbial fermentation.
As an acyl substituent, Guanylic acid takes the form of the prefix guanylyl-.

USES and APPLICATIONS of GUANYLIC ACID:
Biochemical research, flavor potentiator (disodium salt): Guanylic acid is a useful reagent for the chemo- and site-specific reductive amination of N2-guanine oligonucleotides.
Biotechnology and Molecular Biology: As a naturally occurring nucleotide, guanylic acid is essential in genetic research, RNA synthesis studies, nucleic acid chemistry, cell biology, molecular diagnostics, and biotechnology processes.

Guanylic acid is often used in synergy with disodium inosinate; the combination is known as disodium 5′-ribonucleotides.
Guanylic acid is often found in instant noodles, potato chips and snacks, savoury rice, tinned vegetables, cured meats, and packet soup.
As it is a fairly expensive additive, Guanylic acid is usually not used independently of glutamic acid or monosodium glutamate (MSG), which also contribute umami.

If inosinate and guanylate salts are present in a list of ingredients but MSG does not appear to be, the glutamic acid is likely provided as part of another ingredient, such as a processed soy protein complex (hydrolyzed soy protein), autolyzed yeast, or soy sauce.
In the food industry, guanylic acid and its salts are widely recognized for their flavor-enhancing properties.

They contribute a strong umami taste and exhibit a synergistic effect with glutamates, significantly increasing savory flavor intensity.
Due to these characteristics, guanylic acid derivatives are frequently used in seasonings, soups, sauces, snacks, processed foods, and flavoring systems.
Guanylic acid is widely used in the food industry as a flavor-enhancing ingredient due to its ability to intensify umami taste.

Guanylic acid is commonly utilized in combination with glutamates to improve the savory characteristics of processed foods, soups, sauces, seasonings, and snack products.
Guanylic acid and its salts are used to enhance flavor perception while allowing for reduced salt content in food formulations.
Guanylic acid is employed in the production of flavoring systems designed to increase palatability and consumer acceptance.

Guanylic acid is utilized in biotechnology applications, including microbial fermentation and cell culture research.
Guanylic acid is employed in pharmaceutical and life science research for investigations related to nucleotide metabolism and cellular functions.
Guanylic acid is used in laboratory and analytical applications as a reference material and research reagent.

-Nutritional and Fermentation Applications of Guanylic acid:
Guanylic acid may be produced through microbial fermentation and enzymatic processes.
Fermentation-derived GMP is commonly used in food flavor enhancement and nutritional formulations.

-Food Industry Applications of Guanylic acid:
Guanylic acid and its derivatives are extensively used as flavor enhancers.
They intensify savory, meaty, and umami flavors in soups, sauces, seasonings, snack foods, processed meats, instant noodles, ready meals, canned products, and savory food formulations.

One of the most important applications of Guanylic acid involves combination with glutamates.
When used together with monosodium glutamate (MSG), guanylic acid dramatically enhances overall flavor intensity, allowing manufacturers to achieve stronger savory profiles with lower additive levels.

-Flavor and Seasoning Systems use of Guanylic acid:
Guanylic acid is widely used in flavor houses and seasoning production.
Guanylic acid contributes depth, richness, mouthfeel, and lingering savory notes in complex flavor systems.

-Pharmaceutical Applications of Guanylic acid:
Guanylic acid is utilized in biochemical research, pharmaceutical development, and nucleotide-based studies.
Guanylic acid serves as a reference compound in molecular biology, enzymology, and nucleotide metabolism investigations.

BENEFITS of GUANYLIC ACID:
One of the primary benefits of guanylic acid is its powerful flavor-enhancing capability.
Guanylic acid significantly increases umami perception and improves overall taste quality in food products.
Another important benefit is Guanylic acid's synergistic interaction with glutamate compounds.

This synergy allows manufacturers to achieve enhanced savory flavors using lower concentrations of flavoring ingredients.
In biological systems, guanylic acid serves as an essential component of RNA and contributes to numerous metabolic pathways.
Guanylic acid plays a role in genetic information transfer, protein synthesis, cellular regulation, and energy-related biochemical reactions.

Guanylic acid also supports the production of important nucleotide derivatives such as GDP, GTP, and cyclic GMP, which participate in cellular signaling and metabolic control mechanisms.
Because guanylic acid naturally occurs in many foods and living organisms, it is well integrated into biological and nutritional systems.

CHARACTERISTICS of GUANYLIC ACID:
Guanylic acid is one of the fundamental nucleotides found in biological systems.
Guanylic acid serves as a precursor for numerous biologically important compounds including RNA, cyclic GMP, GDP, and GTP.
The molecule is indispensable for genetic information processing, protein synthesis, cellular communication, and metabolic regulation.

A distinctive characteristic of guanylic acid is its remarkable flavor-enhancing capacity.
Guanylic acid produces a strong umami effect and works synergistically with glutamic acid and glutamate salts.

This synergistic action greatly enhances savory flavor perception even at relatively low concentrations.
Because it naturally occurs in meat, fish, mushrooms, yeast extracts, and various plant materials, guanylic acid is considered a naturally occurring flavor contributor in many foods.

SOURCES of GUANYLIC ACID:
Guanylic acid was originally identified as the umami substance in dried shiitake mushroom.
The drying process significantly increases Guanylic acid content with the breakdown of RNA.
Guanylic acid can be found in a number of other mushrooms.
Industrial production is based on fermentation: a bacterium converts sugars into AICA ribonucleotide, which is then converted chemically to Guanylic acid.
Tapioca starch is a possible sugar source.

SYNTHESIS of GUANYLIC ACID:
Under low-temperature conditions, guanosine reacts with a phosphorylating agent (e.g., phosphorus oxychloride POCl3) in an organic solvent (e.g., trimethyl phosphate) to generate the intermediate dichlorophosphate.
Subsequently, this intermediate is hydrolyzed in the presence of water or ice to convert into a monophosphate, thereby yielding the target product, Guanylic acid.

Purification Methods
Crystallise Guanylic acid from water and dry it at 110o.

DE NOVO SYNTHESIS of GUANYLIC ACID:
Guanylic acid synthesis starts with D-ribose 5′-phosphate, a product of the pentose phosphate pathway.
The synthesis proceeds by the gradual formation of the purine ring on carbon-1 of ribose, with CO2, glutamine, glycine, aspartate and one-carbon derivatives of tetrahydrofolate donating various elements towards the building of the ring.
As inhibitor of guanosine monophosphate synthesis in experimental models, the glutamine analogue DON can be used.

cGMP
Guanylic acid can also exist as a cyclic structure known as cyclic Guanylic acid.
Within certain cells the enzyme guanylyl cyclase makes cGuanylic acid from GTP.
cGuanylic acid plays an important role in mediating hormonal signaling.

PHYSICAL and CHEMICAL PROPERTIES of GUANYLIC ACID:
Appearance: White to off-white crystalline powder.
Physical State: Solid.
Odor: Odorless.
Taste: Slight savory or umami taste.
Molecular Weight: 363.22 g/mol.
Color: White.
Solubility in Water: Soluble in water.
Solubility in Organic Solvents: Slightly soluble to insoluble in most organic solvents.
Crystal Form: Crystalline solid.

Hygroscopicity: Slightly hygroscopic.
Density: Approximately 1.9–2.0 g/cm³.
Melting Point: Decomposes upon heating before true melting.
Stability: Stable under normal storage conditions.
Molecular Formula: C10H14N5O8P.
Chemical Structure: Purine nucleotide containing guanine, ribose, and phosphate.
Acidity: Weakly acidic due to the phosphate group.
pKa Values: Multiple ionization constants associated with phosphate functionality.

Ionic Character: Forms negatively charged phosphate species in solution.
Hydrogen Bond Donors: Multiple.
Hydrogen Bond Acceptors: Multiple.
Phosphorylation State: Monophosphate nucleotide.
Biological Activity: Essential RNA component and metabolic intermediate.
Thermal Behavior: Decomposes at elevated temperatures.
Compatibility: Compatible with numerous food, biochemical, and pharmaceutical formulations.
Reactivity: Participates in enzymatic phosphorylation and dephosphorylation reactions.

Chemical formula: C10H14N5O8P
Molar mass: 363.223 g·mol−1
Acidity (pKa): 0.7, 2.4, 6.1, 9.4
ECHA EINECS - REACH Pre-Reg: 201-598-8
FDA UNII: 16597955EP
Nikkaji Web: J10.615A
MDL: MFCD00057066
XlogP3: -4.30 (est)
Molecular Weight: 363.22394200

Formula: C10 H14 N5 O8 P
Chemical Name: Guanylic Acid
Common Name: Guanosine Monophosphate (GMP)
IUPAC Name: [(2R,3S,4R,5R)-5-(2-Amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
CAS Number: 85-32-5
EC Number: 201-602-6
Molecular Formula: C10H14N5O8P
Molecular Weight: 363.22 g/mol

Chemical Class: Purine Nucleotide
PubChem CID: 6804
ChemSpider ID: 6547
Appearance: White crystalline powder
Biological Role: RNA nucleotide and metabolic intermediate
Appearance: white crystalline powder (est)
Assay: 97.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 890.17 °C. @ 760.00 mm Hg (est)

Flash Point: 918.00 °F. TCC (492.20 °C.) (est)
logP (o/w): -2.000
Soluble in:
water, slightly
water, 1.299e+004 mg/L @ 25 °C (est)
Insoluble in:
alcohol

CBNumber: CB6271952
Molecular Formula: C10H14N5O8P
Molecular Weight: 363.22
MDL Number: MFCD00057066
MOL File: 85-32-5.mol
Molecular Weight: 363.22 g/mol
XLogP3: -3.5
Hydrogen Bond Donor Count: 6
Hydrogen Bond Acceptor Count: 10
Rotatable Bond Count: 4
Exact Mass: 363.05799942 Da

Monoisotopic Mass: 363.05799942 Da
Topological Polar Surface Area: 202 Å²
Heavy Atom Count: 24
Formal Charge: 0
Complexity: 598
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 4
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0

Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Melting point: 220 - 223°C
Storage temp.: Keep in dark place, Inert atmosphere, Store in freezer, under -20°C
Solubility: DMSO (Very Slightly, Heated, Sonicated), Water (Slightly, Sonicated)
Form: Solid
Boiling point: 64 °C (Press: 0.05 Torr)
Density: 2.47±0.1 g/cm3 (Predicted)
pKa: 1.86±0.10 (Predicted)
Color: White to Off-White

Odor: odorless
Cosmetics Ingredients Functions: HUMECTANT, SKIN CONDITIONING, SKIN CONDITIONING - EMOLLIENT
InChI: 1S/C10H14N5O8P/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,16-17H,1H2,(H2,19,20,21)(H3,11,13,14,18)
InChIKey: RQFCJASXJCIDSX-UHFFFAOYSA-N
SMILES: O=C(NC(N)=N1)C2=C1N(C=N2)C3C(O)C(C(COP(O)(O)=O)O3)O
LogP: -2.000
CAS DataBase Reference: 85-32-5(CAS DataBase Reference)
FDA UNII: 16597955EP
EPA Substance Registry System: 5'-Guanylic acid (85-32-5)
UNSPSC Code: 12352204
NACRES: NA.21

FIRST AID MEASURES of GUANYLIC ACID:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of GUANYLIC ACID:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.

FIRE FIGHTING MEASURES of GUANYLIC ACID:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of GUANYLIC ACID:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of GUANYLIC ACID:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.

STABILITY and REACTIVITY of GUANYLIC ACID:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available