3D Mol Similar

Adenine

: Iupac Name：7H-purin-6-amine; CAS No.: 73-24-5; Molecular Weight：135.13; Modify Date.: 2022-11-09 02:12; Introduction: Adenine is a purine derivative and a nucleobase with a variety of roles in biochemistry. Target: Nucleoside antimetabolite/analogAdenine is a nucleobase 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), andprotein synthesis, as a chemical component of DNA and RNA. The shape of adenine is complementary to ei View more+

Request For Quotation

1. Names and Identifiers

: 1.1 Name; Adenine; 1.2 Synonyms; 1,9-Dihydro-6H-purin-6-imine 1H-Purin-6-amine 1H-Purine, 6-amino- 1H-Purine-6-amine 4-26-00-03561 6-aminopurine 6-amino-Purine 6H-Purin-6-imine, 1,9-dihydro- 7(9)H-purin-6-ylamine 9H-Adenine 9H-Purin-6-amin 9H-Purin-6-amine 9H-Purin-6-yl-amin 9H-Purine-6-amine Ade Adenin ADENINE FREE BASE PLANT TISSUE CULTURETE STED ADENINE(P) Adeninimine adensoine Crytidine EINECS 200-796-1 Leuco-4 MFCD00041790 Purine, 6-amino- T56 BM DN FN HNJ IZ USAF CB-18 usafcb-18 Vitamin B4 Vitamin- B4 vitaminb4(adenine); View all

1.3 CAS No.: 73-24-5

1.4 CID: 190

1.5 EINECS(EC#): 200-796-1

1.6 Molecular Formula: C5H5N5 (isomer)

1.7 Inchi: InChI=1S/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)

1.8 InChIkey: GFFGJBXGBJISGV-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=NC2=NC=NC(=C2N1)N

1.10 Isomers Smiles: C1=NC2=NC=NC(=C2N1)N

2. Properties

2.1 Density: 1.3795 (rough estimate)

2.1 Melting point: >360 °C(lit.)

2.1 Boiling point: 238.81°C (rough estimate)

2.1 Refractive index: 1.7000 (estimate)

2.1 Flash Point: 220°C

2.1 Precise Quality: 135.054489

2.1 PSA: 80.48000

2.1 logP: -0.09

2.1 Solubility: 0.5 M HCl: soluble20mg/mL, Grade III, colorless to faint yellow or tan

2.2 Appearance: Yellow powder

2.3 Chemical Properties: White to almost white crystalline powder

2.4 Physical Properties: Adenine is a white crystalline substance that is an important biological compound found in deoxyribonucleic acid (DNA), ribonucleic acid (RNA), and adenosine triphosphate (ATP). It was once commonly referred to as vitamin B4 but is no longer considered a vitamin. Adenine is derived from purine. Purine is a heterocyclic compound.

2.5 Color/Form: Powder

2.6 Odor: Odorless

2.7 pKa: 4.12(at 25℃)

2.8 Water Solubility: 0.5 g/L (20 oC)

2.9 Stability: Stable. Moisture-sensitive. Incompatible with strong oxidizing agents.

2.10 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: A nitrogenousbase found in DNA and RNA. Itis also a constituent of certain coenzymesand when combined with the sugar riboseit forms the nucleoside adenosine found inAMP, ADP, and ATP. Adenine has apurine ring structure.

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 24 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501; View all

3.3 History: Adenine is one of the two purines found in DNA and RNA. The other is guanine. Adenine and guanine are called bases in reference to DNA and RNA. A nucleic acid base attached to ribose forms a ribonucleoside. Adenine combined with ribose produces the nucleoside adenosine.

3.4 Purification Methods: Crystallise adenine from distilled water. [Beilstein 26 III/IV 3561.] Adenine Preparation Products And Raw materials Preparation Products

3.5 Usage: local antiseptic

4. Safety and Handling

4.1 Symbol: GHS06

4.1 Hazard Codes: Xn,Xi

4.1 Signal Word: Danger

4.1 Risk Statements: 22-20/21/22

4.1 Safety Statements: 26-36

4.1 Packing Group: III

4.1 Hazard Class: 6.1

4.1 Hazard Declaration: H301

4.1 RIDADR: UN 2811 6.1/PG 3

4.1 Safety Profile: Poison by intraperitoneal route. Moderately toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx,.

4.2 Caution Statement: P301 + P310

4.2 WGK Germany: 3

4.2 RTECS: AU6125000

4.2 Safety: Hazard Codes:?Xi
Risk Statements: 36/37/38?
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36: Wear suitable protective clothing
WGK Germany: 3
RTECS: LZ5776910

4.3 Specification: ? Adenine (CAS NO.73-24-5), its Synonyms are 1,6-Dihydro-6-iminopurine ; 1H-Purin-6-amine ; 1H-Purine, 6-amino ; 3,6-Dihydro-6-iminopurine ; 6-Amino-1H-purine ; 6-Amino-3H-purine ; 6-Amino-7H-purine ; 6-Amino-9H-purine ; 6-Aminopurine ; 9H-Purine, 1,6-dihydro-6-imino- ; Adeninimine . It is white to almost white crystalline powder.

4.4 Toxicity: LD50 orally in rats: 745 mg/kg (Philips)

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H301 Toxic if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : in DMSO-d6

13C NMR : Predict

1H NMR : 90 MHz in CDCl3

1H NMR : Predict

IR : KBr disc

IR : nujol mull

SOLID (0.9 mg / 650 mg KBr DISC)

SOLID (1.4 mg / 360 mg KBr DISC) PURITY - ANALYTICAL

SOLID (SPLIT MULL)

Raman : 4880 A,200 M,powder

Mass

7. Synthesis Route

73-24-5Total: 41 Synthesis Route

87-42-3 270 Suppliers

73-24-5 595 Suppliers

Literatures:
Journal of the American Chemical Society, , vol. 80, p. 3932,3935
Yield: null

56-40-6 925 Suppliers

73-24-5 595 Suppliers

73-40-5 354 Suppliers

Literatures:
Journal of Biological Chemistry, , vol. 177, p. 429
Yield: null

58-61-7 515 Suppliers

532-20-7

73-24-5 595 Suppliers

Literatures:
Journal of Organic Chemistry, , vol. 52, # 14 p. 3113 - 3119
Yield: null

View all

8. Precursor and Product

precursor:

409110-30-1

58-61-7

7664-41-7

911667-45-3

6698-26-6

958-09-8

7732-18-5

5957-04-0

5667-20-9

53-84-9

56-40-6

1198-83-0

84-21-9

623-11-0

5122-36-1

87-42-3

61-19-8

13039-55-9

77287-34-4

753502-74-8

64-19-7

3647-48-1

60-92-4

View all

product :

69-93-2

81408-49-3

21149-26-8

4261-14-7

3691-50-7

24309-36-2

707-98-2

958-09-8

175600-97-2

68217-74-3

43003-87-8

5134-49-6

80681-19-2

22917-81-3

10082-95-8

4230-27-7

75347-16-9

5458-50-4

61-19-8

2715-68-6

68-94-0

14013-11-7

7280-81-1

89760-74-7

View all

9. Other Information

9.0 Merck: 14,152

9.1 BRN: 5777

9.2 Description: adenine is one of the purine nitrogenous bases that composes DNA and RNA; composed of two carbon–nitrogen rings. Adenine bonds with thymine in DNA and with uracil in RNA (see base pairing rule); it is also a major component of other molecules such as adenosine triphosphate.

9.3 Chemical Properties: White to almost white crystalline powder

9.4 Chemical Properties: Adenine is a prominent member of the family of naturally occurring purines. Adenine occurs not only in ribonucleic acids (RNA), and deoxyribonucleic acids (DNA), but in nucleosides, such as adenosine, and nucleotides, such as adenylic acid, which may be linked with enzymatic functions quite apart from nucleic acids. Adenine, in the form of its ribonucleotide, is produced in mammals and fowls endogenously from smaller molecules and no nutritional essentiality is ascribed to it. In the nucleosides, nucleotides, and nucleic acids, the attachment or the sugar moiety is at position 9.
The purines and pyrimidines absorb ultraviolet light readily, with absorption peaks at characteristic frequencies. This has aided in their identification and quantitative determination.

9.5 Physical properties: Adenine is a white crystalline substance that is an important biological compound found in deoxyribonucleic acid (DNA), ribonucleic acid (RNA), and adenosine triphosphate (ATP). It was once commonly referred to as vitamin B₄ but is no longer considered a vitamin. Adenine is derived from purine. Purine is a heterocyclic compound.

9.6 History: Adenine is one of the two purines found in DNA and RNA. The other is guanine. Adenine and guanine are called bases in reference to DNA and RNA. A nucleic acid base attached to ribose forms a ribonucleoside. Adenine combined with ribose produces the nucleoside adenosine.

9.7 Uses: Adenine is used as an active component of boron-deficient media to grow yeast in order to assess whether yeast growth is stimulated by boron. It is useful as a local antiseptic and vitamin B4. Further, it is used in the microbial determination of niacin. It is also employed as a food supplement for adult rats to investigate the effects of dietary adenine overload. In addition to this, it is used in the production of nucleotides of the nucleic acids.

9.8 Uses: local antiseptic

9.9 Uses: Vitamin B4

9.10 Uses: Widespread throughout animal and plant tissues combined with niacinamide, d-ribose, and phosphoric acids; a constituent of nucleic acids and coenzymes, such as codehydrase I and II, adenylic acid, coa laninedehydrase. It is used in microbial determination of niacin; in research on heredity, virus diseases, and cancer.

9.11 Uses: enteric coating

9.12 Uses: A purine nucleobase and a component of DNA

9.13 Definition: A nitrogenous base found in DNA and RNA. It is also a constituent of certain coenzymes and when combined with the sugar ribose it forms the nucleoside adenosine found in AMP, ADP, and ATP. Adenine has a purine ring structure.

9.14 Definition: adenine: A purine derivative. It isone of the major component bases ofnucleotides and the nucleic acidsDNA and RNA.

9.15 Definition: ChEBI: The parent compound of the 6-aminopurines, composed of a purine having an amino group at C-6.

9.16 Synthesis Reference(s): Journal of the American Chemical Society, 88, p. 3829, 1966 DOI: 10.1021/ja00968a028

9.17 General Description: Adenine is a purine nucleobase. It is part of DNA, and RNA. Adenine is also a component of cofactors (NAD, FAD) and signaling molecules (cAMP).

10. Computational chemical data

Molecular Weight: 135.13g/mol
Molecular Formula: C₅H₅N₅
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 135.05449518
Monoisotopic Mass: 135.05449518
Complexity: 127
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 80.5
Heavy Atom Count: 10
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYBjgAAAAAAAAAAAAAAAAAAAAWAAAAAsAAAAAAAAAFgB+AAAHAAQAAAACAgBFwQF8L7JkACgAQZhZACAgC2REKABUaAoVBCASABASEAUBAgIAAJAACAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

What is the role of Adenine in biological processes? Sep 08 2024
Adenine, formerly known as Vitamin B4, is a purine with various functions in biochemistry. It plays a role in cellular respiration as the high-energy molecule adenosine triphosphate (ATP), as well as..
What are the Characteristics, Properties, and Uses of Adenine? Jul 09 2024
Introduction Adenine, a fundamental nucleobase, plays a crucial role in the biochemistry of life. As one of the four nucleobases in DNA, adenine (symbolized as A) pairs with thymine (T) in DNA and wit..
What is the significance of Adenine in biochemistry? May 20 2024
Adenine, a molecule composed of carbon, nitrogen, and hydrogen atoms with a chemical formula of C5H5N5, is a key component in nucleotides when it attaches to ribose and phosphate. Belonging to the pur..
What is the impact of Adenine on health? Oct 05 2023
Adenine, an important alkaloid, plays various roles in the human body. It is a component of DNA and RNA, which are crucial for cellular activities and metabolism. However, both excessive and insuffic..