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2-Azetidinecarboxylic acid, (S)-

HCID 16486
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
2133-34-8
Standard SMILES
O=C(O)[C@@H]1CCN1
InChIKey
IADUEWIQBXOCDZ-VKHMYHEASA-N
Molecular formula
C4H7NO2
Average molar mass
101.1 g/mol
Monoisotopic mass
101.04767847

Overview

(S)-azetidine-2-carboxylic acid is the (S)-enantiomer of azetidine-2-carboxylic acid. It is an enantiomer of a (R)-azetidine-2-carboxylic acid. It is a tautomer of a (S)-azetidine-2-carboxylate zwitterion.

Names & identifiers

Preferred name
2-Azetidinecarboxylic acid, (S)-
IUPAC
(2S)-azetidine-2-carboxylic acid
English name
(S)-(-)-2-Azetidinecarboxylic acid
Molecular formula
C4H7NO2
Molecular weight
101.1

Names & synonyms

(S)-Azetidine-2-carboxylic acid(2S)-azetidine-2-carboxylic acid(S)-2-Azetidinecarboxylic acid2-Azetidinecarboxylic acid, (S)-2-Azetidinecarboxylic acid, (2S)-(S)-(-)-2-azetidine carboxylic acidCHEBI:6198RefChem:25831218-362-52133-34-8L-Azetidine-2-carboxylic acid(S)-(-)-2-Azetidinecarboxylic acid
Show more names
H-AZE-OHL-Azetidine-2-carboxylic Acid [Antagonist of L-Proline]L-H-Aze-OHH-AZE(2)-OH(S)-(-)-2-AzetidinecN,3-Methylene-L-alanineL-AZETIDINECARBOXYLIC ACIDl-2-azetidinecarboxylicaci
Azetidyl-2-carboxylic acidL-Azetidine 2-carboxylic acid(S)-(-)-Azetidine-2-carboxylic acid(L)-AZETIDINE-2-CARBOXYLIC ACIDAzetidine-2-carboxylic acid, L-MFCD000051662-Azetidinecarboxylic acid, L-5GZ3E0L9ZU

Database identifiers

CAS
2133-34-8

Properties

Computed structural properties

XLogP
-2.9
Topological polar surface area
49.3 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
7
Formal charge
0
Complexity
91.7

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Plant Oils and Extracts
Color/FormCRYSTALS FROM 95% HOT METHANOL
SolubilitySOL IN COLD & HOT WATER; PRACTICALLY INSOL IN ABSOLUTE ETHANOL
Optical RotationSPECIFIC OPTICAL ROTATION (WATER C= 3.6): -108 DEG @ 20 °C/D ACIDS
Physical DescriptionWhite to cream powder; [Alfa Aesar MSDS]
Other Experimental PropertiesDISCOLORS AT 200 °C & DARKENS UNTIL 310 °C WHEN HEATING STOPPED; UNSTABLE TO MINERAL ACIDS

Physicochemical properties

Melting point
215 °C · ~215 °C (dec.)
alpha
-125 · -125 º (c=1, water 25 ºC)
Boiling point
189.47 °C · 189.47°C (rough estimate)
Density
1.2245 · 1.2245 (rough estimate)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.

Warning

H315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazards SummaryFetotoxicity, effects on fertility, and teratogenicity observed in intraperitoneal studies of rodents; Subcutaneous LD50 (mouse) = 1,000 mg/kg; [RTECS] May cause irritation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (66.7%)

Toxicology

Interactions · 2 items

THE CHRONIC ADMINISTRATION OF CARBON TETRACHLORIDE TO RATS INDUCED CIRRHOSIS AND INCREASED ALBUMIN SYNTHESIS, BUT SIMULTANEOUS ADMIN OF CARBON TETRACHLORIDE WITH L-AZETIDINE-2-CARBOXYLIC ACID DECR ALBUMIN SYNTHESIS AND ELICITED A RETURN OF SERUM ALBUMIN LEVELS TO NORMAL VALUES.

L-AZETIDINE-2-CARBOXYLIC ACID SEVERELY INHIBITED THE INDUCTION OF NITRATE REDUCTASE BY NITRATE IN RADISH AND CAULIFLOWER LEAF TISSUES WITH A LOW L-PROLINE CONTENT. INHIBITION WAS REVERSED BY SIMULTANEOUS INFILTRATION OF L-PROLINE.

Natural Pollution SourcesFROM CONVALLARIA MAJALIS L (LILY-OF-THE-VALLEY) & POLYGONATUM OFFICINALE MOENSH, LILIACEAE: FOWDEN, BIOCHEM J 64, 323 (1956); FOWDEN, BRYANT, BIOCHEM J 70, 626 (1958).

Chemistry & industry

Pharmacology

Mechanism of Action · 5 items

ALLYLGLYCINE (0.1 MMOL) INHIBITED THE UPTAKE OF 0.1 UMOL 4,5-(3)H-LABELED L-LEUCINE (1 CURIE/MMOLE) AND U-(3)H-LABELED L-PROLINE (266 MCI/MMOLE) BY RAT BRAIN SLICES. LEUCINE UPTAKE WAS NOT LINEAR WITH TIME; PROLINE UPTAKE WAS ALSO INHIBITED BY L-AZETIDINE-2-CARBOXYLIC ACID.

L-AZETIDINE-2-CARBOXYLIC ACID WAS POTENT IN CAUSING AMNESIA OF 1-TRIAL AVOIDANCE CONDITIONING OF THE 2-DAY-OLD CHICK AND IN PREVENTING MECHANICALLY INDUCED SPREADING DEPRESSION IN THE RETINA ISOLATED FROM 2-3 WK-OLD CHICKS. L-AZETIDINE-2-CARBOXYLIC ACID IS INCORPORATED INTO PROTEIN IN PLACE OF L-PROLINE IN SEVERAL PROTEIN-SYNTHESIZING SYSTEMS.

THE ADDITION OF L-AZETIDINE-2-CARBOXYLIC ACID TO THE INCUBATION MEDIUM OF FETAL RAT CALVARIA DECREASED THE INTRACELLULAR FREE PROLINE AND THE RATES OF PROLINE INCORPORATION INTO PROTEIN AND COLLAGEN BY 40-70%. THE ALTERATIONS IN INTRACELLULAR PROLINE CONCN PRODUCED EITHER BY VARYING EXTRACELLULAR PROLINE CONCN OR BY INHIBITING THE UPTAKE OF PROLINE INTO THE INTRACELLULAR POOL MAY CONTRIBUTE TO THE REGULATION OF COLLAGEN SYNTHESIS.

PROLINE PERMEASE FROM PSEUDOMONAS AERUGINOSA OBEYED SATURATION KINETICS & WAS SPECIFIC FOR L-PROLINE. L-AZETIDINE-2-CARBOXYLIC ACID COMPETITIVELY INHIBITED PROLINE UPTAKE. IT WAS ALSO ABLE TO EXCHANGE WITH A PRE-ESTABLISHED LABELED PROLINE INTRACELLULAR POOL.

SIXTEEN-DAY-OLD MOUSE EMBRYONIC ODONTOBLASTS, TREATED FOR 4 DAYS WITH L-2-AZETIDINECARBOXYLIC ACID (50, 100, & 200 GAMMA) WERE POST-MITOTIC, BUT NONPOLARIZED AND DID NOT SECRETE PICROFUCHSIN-POSITIVE SUBSTANCES (COLLAGEN). 18-DAY-OLD EMBRYONIC ODONTOBLASTS TREATED WITH L-2-AZETIDINECARBOXYLIC CONTAINED NO PICROFUCHSIN-POSITIVE SUBSTANCES AND NO COLLAGEN FIBERS OF STRIATION; PREADAMANTOBLASTS WERE POST-MITOTIC BUT NONPOLARIZED.

Uses & manufacturing

Uses · 1 item

2-Azetidinecarboxylic acid: Found in the flowering Lily-of-the-valley and Solomon's seal; Has growth-inhibitory activity on E. coli cultures and germinating seeds; Also a proline analog that produces abnormal proteins with impaired biological activity; [Merck Index]

General Manufacturing InformationACTS AS A PROLINE ANALOG WHERE A STOICHIOMETRIC REPLACEMENT OF PROLINE OCCURRED WITH PRODN OF ABNORMAL PROTEINS HAVING IMPAIRED BIOLOGICAL ACTIVITY...

Related reactions

38 records
New reaction record
HRID 223336 reaction equation
HRID 223336As reactantuspto-grants-1982_10
HRID 344655 reaction equation
HRID 344655As reactantuspto-grants-1991_10
HRID 389863 reaction equation
HRID 389863As reactantuspto-grants-2013_02
HRID 479628 reaction equation
HRID 479628As reactantuspto-grants-2003_11
HRID 482933 reaction equation
HRID 482933As reactantuspto-grants-1986_03
HRID 737165 reaction equation
HRID 737165As reactantuspto-grants-2009_09
HRID 886521 reaction equation
HRID 886521As reactantuspto-grants-2012_08
HRID 973538 reaction equation
HRID 973538As reactantuspto-grants-1991_11
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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
PubChem CID
16486
DTXSID
DTXSID0044020
ChEMBL
CHEMBL1165239
ChEBI
CHEBI:6198
UNII
5GZ3E0L9ZU
EC Number
218-362-5
Nikkaji
J35.234I
refractive index
-122 ° · -122 ° (C=4, H2O)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
solubility
Aqueous Base (Slightly), Methanol (Slightly), Water (Slightly)
pka
2.35 · 2.35±0.20(Predicted)
form
Crystalline Powder or Crystals
color
White to light beige
Water Solubility
5 g/100 · 5 g/100 mL
Merck
14 · 14,908
BRN
80678 · 80678
InChI
1S/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1
InChIKey
IADUEWIQBXOCDZ-VKHMYHEASA-N
SMILES
OC(=O)[C@@H]1CCN1
CAS DataBase Reference
2133 · 2133-34-8(CAS DataBase Reference)
FDA UNII
5 GZ3E0L9ZU · 5GZ3E0L9ZU
UNSPSC Code
12352209 · 12352209
NACRES
32 · NA.32
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P305+P351+P338
PPE
95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
24 · 24/25-36-26
WGK Germany
3 · 3
RTECS
4310500 · CM4310500
Hazard Note
Irritant
HS Code
29339900 · 29339900
Storage Class
11 · 11 - Combustible Solids
Hazardous Substances Data
2133 · 2133-34-8(Hazardous Substances Data)
Toxicity
50 scu-mus: · LD50 scu-mus: 1000 mg/kg 85GDA2 8(1),101,82
Human Toxicity Excerpts · 1 item

INCUBATION OF HUMAN SKIN FIBROBLASTS IN CULTURE WITH L-AZETIDINE-2-CARBOXYLIC ACID (LACA) REDUCED THE RATE OF FIBROBLAST PROLIFERATION AND LOWERED THE PLATING EFFICIENCY. FIBROBLASTS SYNTHESIZED PROCOLLAGEN POLYPEPTIDES WHICH WERE NOT IN A TRIPLE-HELICAL CONFORMATION. THE PROLINE ANALOGS THUS APPEAR TO INHIBIT THE PRODUCTION OF PROCOLLAGEN ON THE POST-TRANSLATIONAL LEVEL BY PREVENTING THE POLYPEPTIDES FROM FOLDING INTO A STABLE TRIPLE-HELICAL CONFORMATION. INHIBITION OF PROCOLLAGEN WAS NOTED IN SCLERODERMA CELLS AS WITH CONTROL FIBROBLAST CULTURES. PROLINE ANALOGS MAY BE USEFUL IN LIMITING EXCESSIVE COLLAGEN DEPOSITION IN SCLERODERMA AND OTHER FORMS OF DERMAL FIBROSIS.

Non-Human Toxicity Excerpts · 5 items

SHOWS GROWTH-INHIBITORY ACTIVITY ON CULTURES OF ESCHERICHIA COLI & ON GERMINATING SEEDS OF DIFFERENT SPECIES IN WHICH IT DOES NOT NORMALLY OCCUR...

...THIS PROLINE ANALOGUE WHICH INHIBITS COLLAGEN ACCUMULATION IN THE CHICK EMBRYO PRODUCES A DECR IN LUNG EPITHELIAL BUDDING. /OTHER INVESTIGATORS/...PRODUCED FUSIONS OF THE VERTEBRAL BODIES OF RAT FETUSES WHOSE MOTHERS WERE GIVEN 300 MG/KG IP ON DAY 8 /OF GESTATION/. THE USE OF 100 MG/DAY FOR 3 DAY PERIODS DURING ORGANOGENESIS CAUSED NO ILL EFFECTS IN THE FETUSES.

L-AZETIDINE-2-CARBOXYLIC ACID WAS EFFECTIVE IN INDUCING POLYTAIL TUBES ABERRATIONS OF THE T-EVEN BACTERIOPHAGE HEAD IN INFECTED ESCHERICHIA COLI B CULTURES.

L-AZETIDINE-2-CARBOXYLIC ACID WAS INJECTED INTO EMBRYONIC EGGS OF THE COMMON FOWL GALLUS DOMESTICUS AT DAILY DOSES OF 350 MUG/EGG ON 1 OR SEVERAL DAYS BETWEEN 8-12 DAYS OF INCUBATION. TREATMENT AT 9 DAYS OF INCUBATION RETARDED EMBRYONIC GROWTH TO THE 12TH DAY, BUT RECOVERY OF GROWTH RATE OCCURRED BY 15 DAYS OF INCUBATION. ADDITION OF L-AZETIDINE-2-CARBOXYLIC ACID TO THE MEDIUM IN WHICH ALREADY DETERMINED STEM CELLS FROM THE QUADRATOJUGAL WERE CULTURED PREVENTED EXPRESSION OF THE CHONDROGENIC PHENOTYPE.

For more Non-Human Toxicity Excerpts (Complete) data for (L)-AZETIDINE-2-CARBOXYLIC ACID (11 total), please visit the HSDB record page.

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
rtecs
CM4310500
hs_code
29339900
Toxicity
LD50 scu-mus: 1000 mg/kg 85GDA2 8(1),101,82
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
hazard_note
Irritant
safety_code
24/25-36-26
Storage Class
11 - Combustible Solids
Hazard statements
H302-H315-H319-H335
Precautionary statements
P261-P305+P351+P338
Hazardous Substances Data
2133-34-8(Hazardous Substances Data)
Applications · 4 items

UsesSpecific proline antagonist. Used in synthesis of abnormally high molecular weight polypeptides.

UsesL-Azetidine-2-carboxylic acid has been used as a:collagen synthesis inhibitorprotein folding antagonistas a standard in liquid chromatography-mass spectrometry

Uses(S)-(-)-2-Azetidinecarboxylic acid is a four-membered ring analog of L-Proline, It is a useful intermediate in the synthesis of polypeptides,Used in synthesis of abnormally high molecular weight polypeptides.

General DescriptionL-Azetidine-2-carboxylic acid is a non-protein amino acid and teratogenic agent. It is toxic in nature.

Upstream & downstream products

Upstream raw materials

Potassium tert-butoxideAcetonitrile2-BromoethanolPotassium carbonatePalladiumL-1-PhenylethylamineTetrahydrofuranDiethyl etherAmmonium chlorideEthyl acetateHydrochloric acidBromoacetonitrileSodium bicarbonateDichloromethaneMethanolDimethyl sulfoxideThionyl chloridePetroleum ether

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
武汉创硕化工科技有限公司180-62205282 18062205282 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
韶远科技(上海)有限公司4000665055 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
阿法埃莎(中国)化学有限公司400-6106006 · [email protected]
艾琪康医药科技(上海)有限公司13661411401 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海相辉医药科技有限公司13761987713 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
深圳虹彩祥根生物科技有限公司+86-0755-89668383 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
上海瀚香生物科技有限公司177-54423994 17754423994 · [email protected]
上海攀鸿化工科技有限公司021-56491756 13512199871 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
上海缤马科技有限公司15262241608 · [email protected]
杭州东帆化学有限公司86-0571-85151182
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
广州科瑞生物技术有限公司20-66003216 18666003216 · [email protected]
武汉海正工贸发展有限公司027-8866 0053/88660577/88660578
艾科试剂4008-755-333 18080918076 · [email protected]
赛默飞世尔科技(中国)有限公司800-810-5118 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
南京诺利斯医药科技有限公司13901585132 · [email protected]
江苏艾康生物医药研发有限公司025-66113011 13913916777 · [email protected]
上海健超生物科技有限公司150-2103-5486 18017383231 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
上海睿升化工科技有限公司+86-021-50935922
上海汇凯化学科技有限公司021-61995394 18916691159 · [email protected]
上海海皋科技有限公司021-57646680 18306277365 · [email protected]
苏州爱玛特生物科技有限公司0512-56316828 4008675858 · [email protected]
上海湄水化工科技有限公司021-60549325 18616193163
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
安徽科迪达化工有限公司0554-2106669 · [email protected]
南京克迪特贸易有限公司025-52164950 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
Labnetwork lnc.+86-27-50766799 +86-18062016861 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海拓目化工有限公司13391076197 · [email protected]

Additional notes

DefinitionChEBI: The (S)-enantiomer of azetidine-2-carboxylic acid.