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thymidine

Thymidine is a deoxyribonucleoside consisting of thymine linked to a deoxyribose sugar, essential in DNA structure and cosmetic skin conditioning.
Chemical Structure

General Material Description

Thymidine, known chemically as 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione, is a deoxyribonucleoside consisting of the nitrogenous base thymine linked to a deoxyribose sugar molecule. This compound is a key component of DNA, contributing to genetic coding and replication. Thymidine appears as a crystalline solid with a molecular formula of C10H14N2O5. It is known by several synonyms including deoxythymidine, 5-methyl-2'-deoxyuridine, and thymine 2-desoxyriboside. As referenced in the ChEBI database, thymidine is biosynthesized in organisms and can be chemically synthesized for research and cosmetic use, particularly in skin conditioning formulations.

Occurrence, Applicability & Potential Uses

Thymidine naturally occurs in biological systems, particularly within DNA of all living cells. It is integral to nucleic acid metabolism and replication processes. In practical applications, thymidine is utilized as a skin conditioning agent in cosmetic products, where it may contribute to cellular repair or regeneration processes. The use of thymidine in cosmetics is regulated under REACH (EU) standards, ensuring safety and compliance within the European market. Though primarily biological, its role extends toward scientific research and specialized industrial applications in cosmetic formulations.

Physico-Chemical Properties Summary

Thymidine exhibits a molecular weight of approximately 242.23 g/mol and presents as a crystalline solid at room temperature. It has moderate water solubility estimated at 7962 mg/L at 25 °C, reflecting considerable hydrophilicity due to multiple hydroxyl groups in its sugar moiety. The compound shows a logP value of about -0.93, indicating low lipophilicity. Its flash point is estimated at 32 °F, limiting its volatility. These physicochemical characteristics influence thymidine's behavior in aqueous and biological systems and affect its formulation in cosmetic products, where solubility and stability in aqueous environments are critical.

FAQ

What is thymidine and what role does it play in biology?
Thymidine is a deoxyribonucleoside composed of the base thymine attached to a deoxyribose sugar. It serves as one of the four nucleoside building blocks of DNA, essential for genetic information storage and replication. Thymidine participates in DNA synthesis and repair by incorporating into DNA strands during cellular division.
How is thymidine commonly sourced and where is it used?
Thymidine is naturally found in all living cells as part of their DNA. It can also be synthetically produced for laboratory research and industrial use. In cosmetic applications, thymidine is used as a skin conditioning agent, potentially supporting cellular processes in skin health. Its usage is controlled under regulations such as REACH (EU) to ensure safe formulation.
What regulatory considerations apply to thymidine, and are there safety concerns?
Thymidine use in cosmetics is regulated under REACH (EU) to maintain safety standards. It is not approved for fragrance or flavor purposes. Toxicological data indicate low acute toxicity, with no significant hazard classifications identified under OSHA HCS (US). Safety data sheets show thymidine has no known hazards under normal handling conditions, but standard precautions should be followed during manufacturing and formulation.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
Metabolomics Database:Search
KEGG (GenomeNet):C00214
HMDB (The Human Metabolome Database):HMDB00273
FooDB:FDB012757
YMDB (Yeast Metabolome Database):YMDB00507
Export Tariff Code:2934.99.9000
MedlinePlusSupp:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report

General Material Information

Preferred name thymidine
Trivial Name Thymidine
Short Description 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
Formula C10 H14 N2 O5
CAS Number 50-89-5
Deleted CAS Number 35902-13-7
ECHA Number 200-070-4
FDA UNII VC2W18DGKR
Nikkaji Number J4.548I
Beilstein Number 89285
MDL MFCD00006537
Bio Activity Summary External link
NMR Predictor External link
Synonyms
  • 1-(2-deoxy-β-D-erythro-pentofuranosyl)-4-hydroxy-5-methyl-
  • 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
  • 1-(2-deoxy-b-D-erythro-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione
  • 1-(2-deoxy-b-D-ribofuranosyl)-5-methyluracil
  • 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-pyrimidine-2,4-dione
  • 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
  • 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-methyl-2,4(1H,3H)-pyrimidinedion
  • 1-[(4S,2R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,3-dihydropyrimidine-2,4-dione
  • 2'- thymidine
  • 2(1H)-pyrimidinone, 1-(2-deoxy-β-D-erythro-pentofuranosyl)-4-hydroxy-5-methyl-
  • 5-methyl-2'-deoxyuridine
  • 5-methyldeoxyuridine
  • 5-methyldeoxyurindine
  • L-thymidine
  • telbivudine
  • thymine-1 2-deoxy-b-D-ribofuranoside
  • dT
  • Thymine 2-desoxyriboside
  • Uridine, 2′-deoxy-5-methyl-
  • β-D-Ribofuranoside, thymine-1 2-deoxy-
  • 2,4(1H,3H)-Pyrimidinedione, 1-(2-deoxy-β-D-erythro-pentofuranosyl)-5-methyl-
  • Deoxythymidine
  • Thymine deoxyriboside
  • 2′-Deoxythymidine
  • Thymidin
  • DThyd
  • 1-(2-Deoxy-β-D-erythro-pentofuranosyl)-5-methyl-2,4(1H,3H)-pyrimidinedione
  • Deoxyribothymidine
  • 5-Methyl-2′-deoxyuridine
  • NSC 21548
  • 10: PN: CN101531718 PAGE: 4 claimed sequence
  • 5: PN: CN104513856 PAGE: 2 claimed sequence
  • β-Thymidine
  • 31: PN: CN108866051 SEQID: 31 claimed sequence
  • Doxribtimine
  • 20: PN: WO2022263569 PAGE: 208 claimed sequence
  • MeSH ID: D013936

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 242.2315826416
Flash Point TCC Value N/a
logP (o/w) -0.93
Solubility
water, 7962 mg/L @ 25 °C (est) Yes

Occurrences

Safety Information

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:
intraperitoneal-mouse LD50 2512 mg/kg
BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Journal of Pharmacology and Experimental Therapeutics. Vol. 207, Pg. 504, 1978.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
cosmetic agents
Recommendation for thymidine usage levels up to:
not for fragrance use.
Recommendation for thymidine flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
ClinicalTrials.gov:search
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA Substance Registry Services (TSCA):50-89-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5789
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
Chemidplus:0000050884
RTECS:XP2071000 for cas# 50-89-5