1-β-D-Arabinofuranosyluracil

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Names

[ CAS No. ]:
3083-77-0

[ Name ]:
1-β-D-Arabinofuranosyluracil

[Synonym ]:
Uracil 1-β-D-Arabinofuranoside
1-Pentofuranosyl-2,4(1H,3H)-pyrimidinedione
4-Hydroxy-1-pentofuranosylpyrimidin-2(1H)-one
1-pentofuranosylpyrimidine-2,4(1H,3H)-dione
Uracil arabinoside
Spongouridine
1-β-D-Arabinofuranosyluracil
1-[3,4-Dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidindion
1-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H- pyrimidine-2,4-dione
1-.β.-D-Arabinofuranosyluracil
2,4(1H,3H)-Pyrimidinedione, 1-pentofuranosyl-
MFCD00065998
1-[3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione
EINECS 221-386-9
2(1H)-pyrimidinone, 4-hydroxy-1-pentofuranosyl-
1-[3,4-Dihydroxy-5-(hydroxyméthyl)tétrahydro-2-furanyl]-2,4(1H,3H)-pyrimidinedione
1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Melting Point ]:
220-222ºC

[ Molecular Formula ]:
C9H12N2O6

[ Molecular Weight ]:
244.201

[ Exact Mass ]:
244.069534

[ PSA ]:
124.78000

[ LogP ]:
-1.61

[ Index of Refraction ]:
1.643

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
YQ8818000
CHEMICAL NAME :
Uracil, 1-beta-D-arabinofuranosyl-
CAS REGISTRY NUMBER :
3083-77-0
BEILSTEIN REFERENCE NO. :
0028749
LAST UPDATED :
199612
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C9-H12-N2-O6
MOLECULAR WEIGHT :
244.23
WISWESSER LINE NOTATION :
T6NVMVJ A- BT5OTJ CQ DQ E1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
90 mg/kg
SEX/DURATION :
female 7-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Rodent - mouse Leukocyte
DOSE/DURATION :
2820 umol/L
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 42,3957,1982

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
22-24/25-36-26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
YQ8818000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • 2,2'-Cyclouridine
  • Uridine
  • 2,2'-Anhydrouridine 3'-carbamate
  • Cyanogen bromide
  • 1-((2R,4S,5R)-3,4-anhydro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-4(1H)-one
  • Cyclocytidine Hydrochloride
  • 2,4(1H,3H)-Pyrimidinedione,1-(2,3,5-tri-O-acetyl-b-D-arabinofuranosyl)-
  • 5-Iodouridine
  • 2α-(Acetoxymethyl)-3β-(acetoxy)-2,3,3aβ,8bβ-tetrahydro-6H-4-oxa-5,8a-diaza-4H-indeno[1,2-b]furan-6-one

DownStream

  • Uracil
  • 2,6-diaminopurine arabinoside
  • 2,4(1H,3H)-Pyrimidinedione,1-b-D-arabinofuranosyldihydro-
  • 2(1H)-Pyrimidinone,3,4-dihydro-4-thioxo-1-(2,3,5-tri-O-acetyl-b-D-arabinofuranosyl)-
  • Thymine-beta-D-arabinofuranoside
  • Vidarabine
  • 2-Fluoroadenosine
  • 2-amino-9-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purine-6-thione
  • 2,4(1H,3H)-Pyrimidinedione,1-b-D-arabinofuranosyl-5-iodo-
  • [3,4-diacetyloxy-5-(2-amino-6-sulfanylidene-3H-purin-9-yl)oxolan-2-yl]methyl acetate

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Related Compounds

  • 2'-methyl-1-β-D-arabinofuranosyluracil
  • 2,2'-anhydro-1-β-D-arabinofuranosyluracil
  • 2,2'-anhydro-1-β-D-arabinofuranosyluracil
  • 1-β-D-Arabinofuranosyluracil 5'-Monophosphate
  • 2',3'-di-O-mesyl-5'-O-trityl-(1-β-D-arabinofuranosyluracil)
  • 2,2'-anhydro-5'chloro-5'-deoxy-1-β-D-arabinofuranosyluracil