Clavulanic acid supplier | CasNO.58001-44-8

Name
Clavulanic acid
EINECS 261-069-2
CAS No. 58001-44-8
Article Data18
CAS DataBase
Density 1.65 g/cm³
Solubility Soluble in water
Melting Point
Formula C₈H₉NO₅
Boiling Point 545.8 °C at 760 mmHg
Molecular Weight 199.163
Flash Point 283.9 °C
Transport Information
Appearance Colorless needle-like crystal
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms (Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid;Acide clavulanique;Acidum clavulanicum;Antibiotic MM 14151;BRL 14151;BRN 0787059;Clavulansaeure;MM 14151;UNII-23521W1S24;
PSA 87.07000
LogP -1.15770

Synthetic route

: 57943-84-7
Benzyl Clavulanate

: 58001-44-8
clavulanic acid

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 0.75h; Ambient temperature;	84%

: 103545-38-6, 103664-39-7, 103664-40-0, 135909-75-0, 135909-76-1
(2RS,5S)-<5-(3)H>Ornithine

A: C8H8(3)HNO5

B: 58001-44-8
clavulanic acid

Conditions

Conditions	Yield
With cultures of Streptomyces clavuligerus (ATCC 27064) in a glycerol-based fermentation medium Product distribution; labelling studies also with incorporation (14)C, acid isolated as p-bromobenzyl ester;

: (2RS,5RS)-<5-(3)H>Ornithine

A: C8H8(3)HNO5

B: 58001-44-8
clavulanic acid

Conditions

Conditions	Yield
With cultures of Streptomyces clavuligerus (ATCC 27064) in a glycerol-based fermentation medium Product distribution; labelling studies also with incorporation (14)C, acid isolated as p-bromobenzyl ester;

: (3R,5R) clavulanate-9-aldehyde

: 58001-44-8
clavulanic acid

Conditions

Conditions	Yield
Streptomyces clavuligerus SC 2;

: 1069-31-4, 3184-13-2, 6211-16-1, 15160-12-0, 16682-12-5, 20724-48-5, 22834-83-9, 26982-21-8, 66837-02-3, 99815-05-1
Ornithin-dihydrochlorid

A: (2S,5S)-3-[2-(2-Acetylamino-acetylamino)-eth-(Z)-ylidene]-7-oxo-4-oxa-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

B: 58001-44-8
clavulanic acid

Conditions

Conditions	Yield
Streptomyces clavuligerus; examination of incorporation by labelled <5-(14)C, 5-(3)H>ornithine;

: 57943-82-5
methyl clavulanate

: 58001-44-8
clavulanic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / sodium hydroxide / H2O / 1.17 h / 0 °C 2: 69 percent / dimethylformamide / 1.5 h / Ambient temperature 3: 84 percent / H2 / palladium on carbon / ethanol / 0.75 h / 760 Torr / Ambient temperature View Scheme

: 57943-81-4
potassium clavulanate

: 58001-44-8
clavulanic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 69 percent / dimethylformamide / 1.5 h / Ambient temperature 2: 84 percent / H2 / palladium on carbon / ethanol / 0.75 h / 760 Torr / Ambient temperature View Scheme

: sodium 3-oxoethylidene-7-oxo-4-oxa-1-azabicyclo-[3.2.0] heptane-2-carboxylate

: 58001-44-8
clavulanic acid

Conditions

Conditions	Yield
With NADPH at 26℃; pH=7.0;

: 4013-94-9
N,N-diisopropyl-1,2-ethanediamine

: 58001-44-8
clavulanic acid

: N,N'-diisopropylethylenediammonium diclavulanate

Conditions

Conditions	Yield
In methanol; water; ethyl acetate for 0.25h;	96%
In ethyl acetate; isopropyl alcohol	84%
In methanol; ethyl acetate	81%

: 3378-72-1
N-tert-butylbenzylamine

: 58001-44-8
clavulanic acid

: C8H9NO5*C11H17N

Conditions

Conditions	Yield
In ethyl acetate	83%
In ethanol; ethyl acetate for 1h;	68%
In ethyl acetate; isopropyl alcohol	67%

: 768-94-5
1-Adamantanamine

: 58001-44-8
clavulanic acid

: 66069-33-8
(2R,5R)-3-[2-Hydroxy-eth-(Z)-ylidene]-7-oxo-4-oxa-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; compound with adamantan-1-ylamine

Conditions

Conditions	Yield
In ethyl acetate	81%
In ethanol; ethyl acetate	80%
In methanol; ethyl acetate for 1h;	76%
In ethyl acetate; isopropyl alcohol	76%

: 75-64-9
tert-butylamine

: 58001-44-8
clavulanic acid

: 66069-34-9
clavulanic acid tert-butylamine

Conditions

Conditions	Yield
In ethyl acetate	81%
In ethyl acetate; isopropyl alcohol for 1h;	77%
In ethanol; ethyl acetate	43%
Stage #1: clavulanic acid With ammonium sulfate In water; ethyl acetate at 5℃; pH=1.30; Stage #2: tert-butylamine In methanol; ethyl acetate at 5℃; for 2h; pH-value; Concentration;

: 107-45-9
tert-Octylamine

: 58001-44-8
clavulanic acid

: 66069-32-7
(2R,5R)-3-[2-Hydroxy-eth-(Z)-ylidene]-7-oxo-4-oxa-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid; compound with 1,1,3,3-tetramethyl-butylamine

Conditions

Conditions	Yield
In ethyl acetate	80%
In ethyl acetate; isopropyl alcohol for 1h;	67%
In ethanol; ethyl acetate	35%

: 58001-44-8
clavulanic acid

: 83670-77-3
methyl-4-aza-8-hydroxy-6-oxo-oct-2-enoate

Conditions

Conditions	Yield
With methanol; diethylamine for 0.166667h; Ambient temperature;	78%

: 186581-53-3, 908094-01-9
diazomethane

: 58001-44-8
clavulanic acid

: 57943-82-5
methyl clavulanate

Conditions

Conditions	Yield
In ethanol Ambient temperature;	75%

: 58001-44-8
clavulanic acid

: 477947-66-3
9-chloro-9-deoxyclavulanic acid

Conditions

Conditions	Yield
With pyridine; methanesulfonyl chloride In acetonitrile at 25℃; for 24h;	75%

: 100-46-9
benzylamine

: 58001-44-8
clavulanic acid

: 62868-57-9
N-benzylclavulanamide

Conditions

Conditions	Yield
With sodium hydroxide; dicyclohexyl-carbodiimide In tetrahydrofuran; dichloromethane; ethyl acetate	67%

: 111-74-0
N,N'-diethylethylenediamine

: 58001-44-8
clavulanic acid

: C6H16N2*2C8H9NO5

Conditions

Conditions	Yield
In ethanol; ethyl acetate for 0.5h;	61%

: 908093-98-1
diazodiphenylmethane

: 58001-44-8
clavulanic acid

: 64018-86-6
benzhydryl clavulanate

Conditions

Conditions	Yield
In tetrahydrofuran Ambient temperature;	60%

: 58001-44-8
clavulanic acid

: 108-95-2
phenol

: 57943-88-1
phenyl clavulanate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In acetonitrile Ambient temperature;	59%

: 140-28-3
N,N'-Dibenzylethylenediamine

: 58001-44-8
clavulanic acid

: 2C8H9NO5*C16H20N2

Conditions

Conditions	Yield
In ethanol; ethyl acetate for 1h;	54%
In ethyl acetate; isopropyl alcohol	31%
In ethyl acetate	3%

: 33966-50-6
SEC-BUTYLAMINE

: 58001-44-8
clavulanic acid

: C4H11N*C8H9NO5

Conditions

Conditions	Yield
In ethanol; ethyl acetate for 1h;	52.6%
In ethyl acetate; isopropyl alcohol	52%
In ethyl acetate	8%

: 103-74-2
2-(2-Hydroxyethyl)pyridine

: 58001-44-8
clavulanic acid

: 91022-06-9
2-(2-pyridyl)ethyl clavulanate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In acetonitrile Ambient temperature;	50%

: 110-18-9
N,N,N,N,-tetramethylethylenediamine

: 58001-44-8
clavulanic acid

: N,N,N',N'-tetramethylethylenediammonium diclavulanate

Conditions

Conditions	Yield
In ethyl acetate; isopropyl alcohol for 1h;	37%
In ethyl acetate	30%

: 58001-44-8
clavulanic acid

A: 58243-07-5
methyl (E)-3-(diethylamino)-2-propenoate

B: 83670-73-9
methyl 3-(2-hydroxyethyl)-pyrrole-4-carboxylate

C: 83670-77-3
methyl-4-aza-8-hydroxy-6-oxo-oct-2-enoate

Conditions

Conditions	Yield
With diethylamine In methanol for 48h; Ambient temperature;	A 20% B 14% C 18%
With Diethyl amine In methanol for 48h; Ambient temperature;	A 20% B 14% C 18%

...Expand

: 106-45-6
para-thiocresol

: 58001-44-8
clavulanic acid

: 91022-05-8
p-tolyl thioclavulanate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In acetonitrile Ambient temperature;	17%

: 58001-44-8
clavulanic acid

A: (E)-(5R)-3-(2-hydroxyethylidene)-4-oxa-1-azabicyclo<3.2.0>heptan-7-one

B: (Z)-(5R)-3-(2-hydroxyethylidene)-4-oxa-1-azabicyclo<3.2.0>heptan-7-one

Conditions

Conditions	Yield
With mercury(II) diacetate In 1,2-dimethoxyethane 1) r.t., 15 min, 2) 90-95 deg C (bath), 20 min;	A 5% B 5.5%

: 58001-44-8
clavulanic acid

: 71019-00-6
(5R)-7-oxo-3-vinyl-4-oxa-1-azabicyclo[3.2.0]hept-2-ene

Conditions

Conditions	Yield
With N,N-dimethyl-formamide dimethyl acetal In tetrahydrofuran
With N,N-dimethyl-formamide dimethyl acetal In tetrahydrofuran for 0.133333h; Ambient temperature; Yield given;
With N,N-dimethyl-formamide dimethyl acetal

: 501-53-1
benzyl chloroformate

: 58001-44-8
clavulanic acid

: 92632-80-9
1-benzyloxycarbonylamino-4-hydroxybutan-2-one

Conditions

Conditions	Yield
With hydrogenchloride; water; sodium hydrogencarbonate 1.) 2 h, 2.) water, THF, ice-cooling, 40 min; Yield given. Multistep reaction;

: 937-14-4
3-chloro-benzenecarboperoxoic acid

: 58001-44-8
clavulanic acid

: 71916-37-5
(Z)-(3S,5R)-2-(2-hydroxyethylidene)-3-(m-chlorobenzoyloxy)clavam

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In 1,2-dimethoxyethane; dichloromethane 1.) 0 deg C, 3 h, 2.) room temperature, 15 h;	60 mg

: 67-56-1
methanol

: 58001-44-8
clavulanic acid

A: 57943-82-5
methyl clavulanate

B: 88367-33-3
(Z)-(2R)-5-(2-hydroxyethylidene)-2-methoxycarbonylmethyl-2,5-dihydro-oxazole

C: 88391-46-2
(Z)-(3S,5R)-2-(2-hydroxyethylidene)-3-methoxyclavam

Conditions

Conditions	Yield
With triethylamine at -30℃; for 0.833333h; electrolysis: platinum electrodes, I=200-250 mA;	A 5 mg B 75 mg C 10 mg
With triethylamine at -30℃; for 0.833333h; electrolysis: platinum electrodes, current 200-250 mA;	A 5 mg B 75 mg C 10 mg

...Expand

: 67-56-1
methanol

: 58001-44-8
clavulanic acid

A: 57943-82-5
methyl clavulanate

B: 88391-46-2
(Z)-(3S,5R)-2-(2-hydroxyethylidene)-3-methoxyclavam

C: 71916-39-7, 88391-48-4, 88391-49-5
(E)-(3S,5R)-3-acetoxy-2-formylmethyleneclavam

D: 88391-49-5
(Z)-(3S,5R)-3-acetoxy-2-formylmethyleneclavam

Conditions

Conditions	Yield
With triethylamine at -30℃; for 0.833333h; Product distribution; electrolysis, platinum electrodes, current 200-250 mA; reactions of oxidative decarboxylation ( electrolysis, with Pb(OAc)4, decarboxylative rearrangement of diacyl peroxide) of clavulanic acid and its methyl ether;	A 5 mg B 10 mg C n/a D n/a

...Expand

: 546-67-8
lead(IV) tetraacetate

: 58001-44-8
clavulanic acid

A: 88391-50-8
(Z)-(3S,5R)-3-acetoxy-2-(2-hydroxyethylidene)clavam

B: 88391-47-3
(Z)-(3S,5R)-3-acetoxy-2-(2-acetoxyethylidene)clavam

C: 71916-39-7, 88391-48-4, 88391-49-5
(E)-(3S,5R)-3-acetoxy-2-formylmethyleneclavam

D: 88391-49-5
(Z)-(3S,5R)-3-acetoxy-2-formylmethyleneclavam

Conditions

Conditions	Yield
In 1,2-dimethoxyethane; benzene at 70℃; for 0.333333h;	A 145 mg B 20 mg C n/a D n/a
In 1,2-dimethoxyethane; benzene at 70℃; for 0.333333h; Yields of byproduct given;	A 145 mg B 20 mg C n/a D n/a
In 1,2-dimethoxyethane; benzene at 70℃; for 0.333333h; Yield given. Title compound not separated from byproducts;	A 145 mg B 20 mg C n/a D n/a

...Expand

Clavulanic acid History

Clavulanic acid was discovered around 1974/75 by British scientists working at the drug company Beecham. After several attempts, Beecham finally filed for US patent protection for the drug in 1981, and U.S. Patents 4,525,352, 4,529,720 and 4,560,552 were granted in 1985.

Clavulanic acid Specification

The Clavulanic acid with CAS registry number of 58001-44-8 is also known as 4-Oxa-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 3-(2-hydroxyethylidene)-7-oxo-, (2R,3Z,5R)-. The IUPAC name is (2R,3Z,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid. It belongs to product categories of Antibiotics. Its EINECS registry number is 261-069-2. In addition, the formula is C₈H₉NO₅ and the molecular weight is 199.16. This chemical is a colorless needle-like crystal that soluble in water. It is a beta-lactamase inhibitor and used to overcome resistance in bacteria. What's more, it can be prepared by alkylation and chlorination decarboxylation reaction of 3-methylthiopropyllactam.

Physical properties about Clavulanic acid are: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 1; (4)ACD/KOC (pH 7.4): 1; (5)#H bond acceptors: 6; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 3; (8)Index of Refraction: 1.644; (9)Molar Refractivity: 43.56 cm³; (10)Molar Volume: 120.2 cm³; (11)Surface Tension: 82.2 dyne/cm; (12)Density: 1.65 g/cm³; (13)Flash Point: 283.9 °C; (14)Enthalpy of Vaporization: 94.82 kJ/mol; (15)Boiling Point: 545.8 °C at 760 mmHg; (16)Vapour Pressure: 3.45E-14 mmHg at 25 °C.

Uses of Clavulanic acid: it is used to produce 2-(2-pyridyl)ethyl clavulanate by reaction with 2-pyridin-2-yl-ethanol. The reaction occurs with reagent dicyclohexylcarbodi-imide and solvent acetonitrile with ambient temperature. The yield is about 50%.

Clavulanic acid is used to produce 2-(2-pyridyl)ethyl clavulanate by reaction with 2-pyridin-2-yl-ethanol.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing, gloves and eye/face protection. Avoid contact with skin and eyes. After using it, take off immediately all contaminated clothing. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1C2N(C1=O)C(C(=CCO)O2)C(=O)O
2. Isomeric SMILES: C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O
3. InChI: InChI=1S/C8H9NO5/c10-2-1-4-7(8(12)13)9-5(11)3-6(9)14-4/h1,6-7,10H,2-3H2,(H,12,13)/b4-1-/t6-,7-/m1/s1
4. InChIKey: HZZVJAQRINQKSD-PBFISZAISA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LD50	intraperitoneal	1531mg/kg (1531mg/kg)	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 590, 1985.
mouse	LD50	intravenous	4gm/kg (4000mg/kg)	"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 4(1), Pg. 129, 1980.
mouse	LD50	oral	4526mg/kg (4526mg/kg)	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 590, 1985.
mouse	LD50	subcutaneous	2185mg/kg (2185mg/kg)	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 590, 1985.
rat	LD50	intraperitoneal	1399mg/kg (1399mg/kg)	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 590, 1985.
rat	LD50	oral	7936mg/kg (7936mg/kg)	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 590, 1985.
rat	LD50	subcutaneous	1393mg/kg (1393mg/kg)	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 590, 1985.

Product Name

Clavulanic acid

Synthetic route

Clavulanic acid History

Clavulanic acid Specification

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