3,4-Dehydro-L-proline

Names

[ Name ]:
3,4-Dehydro-L-proline

[Synonym ]:
3,4-Dehydro-L-proline
(S)-2,5-Dihydro-1H-pyrrole-2-carboxylic acid
(2S)-2,5-dihydro-1H-pyrrole-2-carboxylic acid
EINECS 223-738-7
MFCD00153487

Chemical & Physical Properties

[ Density]:
1.252g/cm3

[ Boiling Point ]:
279.3ºC at 760mmHg

[ Melting Point ]:
239-241ºC (dec.)

[ Molecular Formula ]:
C₅H₇NO₂

[ Molecular Weight ]:
113.11

[ Flash Point ]:
122.7ºC

[ Exact Mass ]:
113.04800

[ PSA ]:
49.33000

[ Vapour Pressure ]:
0.00108mmHg at 25°C

[ Index of Refraction ]:
1.521

[ Storage condition ]:
-15°C

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UX9371345

CHEMICAL NAME :: 1H-Pyrrole-2-carboxylic acid, 2,5-dihydro-, (S)-

CAS REGISTRY NUMBER :: 4043-88-3

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C5-H7-N-O2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 617 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 26,426,1973 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 720 mg/kg/9D-I

TOXIC EFFECTS :: Liver - jaundice, other or unclassified Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

REFERENCE :: TOXID9 Toxicologist. (Soc. of Toxicology, Inc., 475 Wolf Ledge Parkway, Akron, OH 44311) V.1- 1981- Volume(issue)/page/year: 3,127,1983

Safety Information

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

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UX9371345

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

(2S)-2,5-dihydro-1H-pyrrole-1,2-dicarboxylic acid 2-methyl 1-(phenylmethyl) ester
methyl 1-benzyloxycarbonyl-(4S)-phenylseleno-(2S)-pyrrolidinylcarboxylate

DownStream

(S)-1-(tert-Butoxycarbonyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid
Fmoc-3,4-dehydro-L-proline

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Transport and signaling via the amino acid binding site of the yeast Gap1 amino acid transceptor.

Nat. Chem. Biol. 5 , 45-52, (2009)

Transporter-related nutrient sensors, called transceptors, mediate nutrient activation of signaling pathways through the plasma membrane. The mechanism of action of transporting and nontransporting tr...

Many amino acid substitutions in a hypoxia-inducible transcription factor (HIF)-1alpha-like peptide cause only minor changes in its hydroxylation by the HIF prolyl 4-hydroxylases: substitution of 3,4-dehydroproline or azetidine-2-carboxylic acid for the proline leads to a high rate of uncoupled 2-oxoglutarate decarboxylation.

J. Biol. Chem. 279(53) , 55051-9, (2004)

Three human prolyl 4-hydroxylases (P4Hs) regulate the hypoxia-inducible transcription factors (HIFs) by hydroxylating a Leu-Xaa-Xaa-Leu-Ala-Pro motif. We report here that the two leucines in the Leu-G...

Overexpression of decorin by rat arterial smooth muscle cells enhances contraction of type I collagen in vitro.

Arterioscler. Thromb. Vasc. Biol. 24(1) , 67-72, (2004)

Overexpression of decorin reduces neointimal thickening in balloon-injured carotid arteries of rats by decreasing the volume of neointimal extracellular matrix (ECM). We examined the hypothesis that d...

3,4-DEHYDRO-L-PROLINE HCI
Boc-3,4-Dehydro-L-proline
Boc-3,4-Dehydro-L-proline
Fmoc-3,4-dehydro-L-proline
Boc-3,4-dehydro-L-proline methyl ester
3,4-DEHYDRO-L-PROLINE AMIDE HYDROCHLORIDE
3-Hydroxypyridine-2,5-dicarbaldehyde
4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
(4-Methyl-tetrahydro-furan-2-yl)-methanol
N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
tert-Butyl-DL-alanine
N-(1-cyano-1,2,2-trimethylpropyl)-2-[(2-methylphenyl)sulfanyl]acetamide