CAS No.58001-44-8,Clavulanic acid Suppliers

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Basic Information

Molecular Structure:
CAS No.:	58001-44-8
Name:	Clavulanic acid
Article Data:	18

Formula:	C₈H₉NO₅
Molecular Weight:	199.163
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;
EINECS:	261-069-2
Density:	1.65 g/cm³
Boiling Point:	545.8 °C at 760 mmHg
Flash Point:	283.9 °C
Solubility:	Soluble in water
Appearance:	Colorless needle-like crystal
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%

Raw Materials

57943-82-5

57943-81-4

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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.

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.