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L(+)-Isovaline monohydrate

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Origin: China

Cas No: 595-40-4

Specification: 99%min

Min order Quantity: 1 /kg

Supply Ability: 80 mt/month

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Products Specification
Product Description

Property
CAS No.: 595-40-4 Formula: C5H13NO3 Molecular Weight: 135.16200

Description
Isovaline is a rare amino acid transported to earth by the Murchison meteorite, which landed in Australia in 1969. The discovery of isovaline in the biosphere demonstrates an extraterrestrial origin of amino acids and has been linked to the homochirality of life on earth suggesting a role in the origin of life.
The structure of isovaline is similar to the amino acids GABA and glycine, the chief inhibitory neurotransmitters in the mammalian central nervous system. Isovaline acts as an analgesic in mice by activating peripheral GABAB receptors. In a mouse model of osteoarthritis isovaline restored mobility, suggesting inhibition of nociception by isovaline in the synovial membrane of the mouse knee.
Isovaline does not cross the blood-brain barrier and does not enter into the brain or spinal cord. Drugs such as opioids cross the blood-brain barrier to produce analgesia but often produce confusion, sedation and addiction.
Isovaline acts downstream to the cyclooxygenase system that NSAIDs inhibit, suggesting a means to avoid adverse effects such as irritation of the gastrointestinal system.
This novel first-in-class compound has potential for treatment of acute and chronic pain, without the negative side effects associated with other commonly used analgesics.

Basic Info

Chemical Name L(+)-Isovaline monohydrate

Synonyms
L-Isovaline;

CAS No. 595-40-4

Molecular Formula C5H13NO3

Molecular Weight 135.16200

PSA 72.55000

LogP 0.83440

Properties

Density 1.07 g/cm3

Boiling Point 213.6ºC at 760 mmHg

Flash Point 83ºC

Refractive Index 1.465

Safety Info

Safety Statements S24/25

Synthesis Route
(3S,5aR,6aS,7aS)-3-ethyl-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-2(3H)-one→L(+)-Isovaline monohydrate
(3S,6R)-N-1-(tert-butoxycarbonyl)-3-ethyl-6-isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone→L(+)-Isovaline monohydrate
(R)-2-Ethyl-2-methyl-malonic acid mono-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester→L(+)-Isovaline monohydrate

Precursor
(3S,5aR,6aS,7aS)-3-ethyl-5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethylbicyclo[4.1.0]hept-1(6)eno[3,4-b][1,4]oxazin-2(3H)-one
(1R,3R,4S)-8-phenyl-p-menthan-3-yl (2'S)-2'-amino-2'-methylbutanoate
(3S,6R)-N-1-(tert-butoxycarbonyl)-3-ethyl-6-isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone
(R)-2-Ethyl-2-methyl-malonic acid mono-[(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl] ester

Downstream Product
methyl (2S)-2-amino-2-methylbutanoate,hydrochloride
(S)-N-BOC-alpha-Ethylalanine
2-hydroxy-2-methylbutyric acid
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-isovaline