adenine
1H-purin-6-amine
 
Notes:
a purine base and a fundamental unit of adenine nucleotides. a purine base and a fundamental unit of adenine nucleotides. Widespread throughout animal and plant tissue, purine components of DNA, RNA, and coenzymes. Vitamin Adenine (sometimes known as vitamin B4) combines with the sugar ribose to form adenosine, which in turn can be bonded with from one to three phosphoric acid units, yielding AMP, ADP and ATP . These adenine derivatives perform important functions in cellular metabolism. Adenine is one of four nitrogenous bases utilized in the synthesis of nucleic acids. A modified form of adenosine monophosphate (cyclic AMP) is an imporant secondary messenger in the propagation of many hormonal stimuli. Adenine is an integral part of the structure of many coenzymes. Adenosine (adenine with a ribose group) causes transient heart block in the AV node of the heart. In individuals suspected of suffering from a supraventricular tachycardia (SVT), adenosine is used to help identify the rhythm. Certain SVTs can be successfully terminated with adenosine.; Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose. It forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between chemical reactions.; Adenine is a nucleobase (a purine derivative) with a variety of roles in biochemistry including cellular respiration, in the form of both the energy-rich adenosine triphosphate (ATP) and the cofactors nicotinamide adenine dinucleotide (NAD) and flavin adenine dinucleotide (FAD), and protein synthesis, as a chemical component of DNA and RNA. The shape of adenine is complementary to either thymine in DNA or uracil in RNA.; Adenine is a purine base. Adenine is found in both DNA and RNA. Adenine is a fundamental component of adenine nucleotides. Adenine forms adenosine, a nucleoside, when attached to ribose, and deoxyadenosine when attached to deoxyribose; Adenine is one of the two purine nucleobases (the other being guanine) used in forming nucleotides of the nucleic acids. In DNA, adenine binds to thymine via two hydrogen bonds to assist in stabilizing the nucleic acid structures. In RNA, which is used in the cytoplasm for protein synthesis, adenine binds to uracil.; In older literature, adenine was sometimes called Vitamin B4. It is no longer considered a true vitamin or part of the Vitamin B complex. However, two B vitamins, niacin and riboflavin, bind with adenine to form the essential cofactors nicotinamide adenine dinucleotide (NAD) and flavin adenine dinucleotide (FAD), respectively. Hermann Emil Fischer was one of the early scientists to study Adenine.; it forms adenosine triphosphate (ATP), a nucleotide, when three phosphate groups are added to adenosine. Adenosine triphosphate is used in cellular metabolism as one of the basic methods of transferring chemical energy between chemical reactions.; Purine inborn errors of metabolism (IEM) are serious hereditary disorders, which should be suspected in any case of neonatal fitting, failure to thrive, recurrent infections, neurological deficit, renal disease, self-mutilation and other manifestations. Investigation usually starts with uric acid (UA) determination in urine and plasma. (OMIM 300322, 229600, 603027, 232400, 232600, 232800, 201450, 220150, 232200, 162000, 164050, 278300). (PMID: 17052198, 17520339)
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7H-purin-6-amine (Click)
CAS Number: 73-24-5Picture of molecule
Other: 22051-90-7
ECHA EINECS - REACH Pre-Reg: 200-796-1
FDA UNII: JAC85A2161
Nikkaji Web: J5.257D
MDL: MFCD00041790
XlogP3: -0.10 (est)
Molecular Weight: 135.12985000
Formula: C5 H5 N5
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: cosmetic ingredient for skin conditioning
 
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Physical Properties:
Appearance: white crystalline powder (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 360.00 °C. @ 760.00 mm Hg
Boiling Point: 553.00 to  554.00 °C. @ 760.00 mm Hg (est)
Flash Point: 613.00 °F. TCC ( 322.70 °C. ) (est)
logP (o/w): -0.090
Soluble in:
 water, 1030 mg/L @ 25 °C (exp)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: skin conditioning
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Suppliers:
George Uhe Company
Adenine Compounds
Penta International
ADENINE USP
Santa Cruz Biotechnology
For experimental / research use only.
Adenine, Cell Culture 99%
Sigma-Aldrich: Aldrich
For experimental / research use only.
Adenine 99%
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50  227 mg/kg
LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: MUSCLE WEAKNESS
Toxicology and Applied Pharmacology. Vol. 47, Pg. 229, 1979.

intraperitoneal-rat LD50  198 mg/kg
BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Journal of Pharmacology and Experimental Therapeutics. Vol. 104, Pg. 20, 1952.

oral-mouse LD50  783 mg/kg
Drugs in Japan Vol. 6, Pg. 19, 1982.

intravenous-mouse LD50  > 30 mg/kg
Drugs in Japan Vol. 6, Pg. 20, 1982.

intraperitoneal-mouse LD50  100 mg/kg
National Technical Information Service. Vol. AD277-689

Dermal Toxicity:
subcutaneous-mouse LDLo 1000 mg/kg
Annals of the New York Academy of Sciences. Vol. 60, Pg. 251, 1954.

Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: cosmetic ingredient for skin conditioning
Recommendation for adenine usage levels up to:
 not for fragrance use.
 
Recommendation for adenine flavor usage levels up to:
 not for flavor use.
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Safety References:
European Food Safety Authority (EFSA) reference(s):
Scientific Report of EFSA on the risk assessment of salts of authorised acids, phenols or alcohols for use in food contact materials [1]
View page or View pdf
EPI System: View
Chemical Carcinogenesis Research Information System: Search
AIDS Citations: Search
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Toxicology Citations: Search
EPA GENetic TOXicology: Search
Env. Mutagen Info. Center: Search
NLM Developmental and Reproductive Toxicity: Search
EPA Substance Registry Services (TSCA): 73-24-5
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 190
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 7H-purin-6-amine
Chemidplus: 0000073245
RTECS: AU6125000 for cas# 73-24-5
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References:
 7H-purin-6-amine
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 73-24-5
Pubchem (cid): 190
Pubchem (sid): 134972794
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
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KEGG (GenomeNet): C00147
HMDB (The Human Metabolome Database): HMDB00034
FooDB: FDB012266
YMDB (Yeast Metabolome Database): YMDB00887
Export Tariff Code: 2933.90.9500
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 apple root
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 celery plant
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 mugwort plant
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 potato plant
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 rice seed
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 soybean seed
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 soybean sprout
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 tea leaf
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 wheat petiole
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Synonyms:
9H-adenine
 adeninimine
6-amino-purine
1,6-dihydro-6-iminopurine
1,9-dihydro-6H-purin-6-imine
 leuco-4
 pedatisectine B
1H-purin-6-amine
7H-purin-6-amine
6H-purin-6-imine, 1,9-dihydro-
1H-purine-6-amine
1H-purine, 6-amino-
 vitamin B4
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Articles:
PubMed: Irreversible inactivation of snake venom l-amino acid oxidase by covalent modification during catalysis of l-propargylglycine.
PubMed: Altered Ca(2+) regulation of Yop secretion in Yersinia enterocolitica after DNA adenine methyltransferase overproduction is mediated by Clp-dependent degradation of LcrG.
PubMed: Laboratory-evolved vanillyl-alcohol oxidase produces natural vanillin.
PubMed: Role of riboflavin in beer flavor instability: determination of levels of riboflavin and its origin in beer by fluorometric apoprotein titration.
PubMed: Neuromuscular disorder associated with a defect in mitochondrial energy supply.
PubMed: Enzymatic removal of diacetyl from beer. 3. Enzyme protection and regeneration of cofactor.
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