Pinonic acid

Base Information

• Chemical Name: Pinonic acid
• CAS No.: 473-72-3
• Molecular Formula: C10H16 O3
• Molecular Weight: 184.235
• European Community (EC) Number: 207-471-3,627-342-9
• NSC Number: 609391,96748,46248,29469
• DSSTox Substance ID: DTXSID60874123
• Nikkaji Number: J67.758B
• Mol file: 473-72-3.mol

Synonyms:Pinonic acid;473-72-3;2-(3-acetyl-2,2-dimethylcyclobutyl)acetic acid;cis-Pinonic acid;61826-55-9;Cyclobutaneacetic acid, 3-acetyl-2,2-dimethyl-;EINECS 207-471-3;cis-3-Acetyl-2,2-dimethylcyclobutylacetic acid;NSC 29469;AI3-19190;NSC29469;3-ACETYL-2,2-DIMETHYLCYCLOBUTANEACETIC ACID;NSC609391;Cyclobutaneacetic acid,2-dimethyl-;(1R)-3alpha-Acetyl-2,2-dimethylcyclobutane-1alpha-acetic acid;Cyclobutaneacetic acid, 3-acetyl-2,2-dimethyl-, (1R,3R)-rel-;(+) Pinonic acid;(+)-Pinonic acid;SCHEMBL611079;DTXSID60874123;NSC46248;NSC96748;NSC 45643;NSC-29469;NSC-46248;NSC-96748;AKOS004120644;NSC-609391;SB45648;LS-55824;CS-0345782;EN300-296222;(3-acetyl-2,2-dimethyl-cyclobutyl)-acetic acid

Chemical Property of Pinonic acid

Chemical Property:

• Melting Point: 104-107℃
• Boiling Point: 305.2°Cat760mmHg
• Flash Point: 152.6°C
• PSA: 54.37000
• Density: 1.065g/cm³
• LogP: 1.71240
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 3.686g/L(0 oC)
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 184.109944368
• Heavy Atom Count: 13
• Complexity: 243

Purity/Quality:

98%min ^*data from raw suppliers

PinonicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C1CC(C1(C)C)CC(=O)O
• Uses: Pinonic Acid is identified as a low-volatility species produced in the atmosphere when α-pinene undergoes reactions with ozone, OH radical or NO3 radical.

Technology Process of Pinonic acid

There total 61 articles about Pinonic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(-)-α-pinene (7785-26-4,25766-18-1) → (1'R,3'R)-2-(3'-acetyl-2',2'-dimethylcyclobutyl)acetic acid (473-72-3,17879-35-5,61376-92-9,61826-55-9,64396-97-0,127062-09-3,52305-34-7)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 24h;

DOI:10.1021/jo991773c

Reference yield: 96.0%

3(2),3(2),7-trimethyl-2,5-dioxo-6-oxa-3(1,3)-cyclobutanaoctaphane → (1'R,3'R)-2-(3'-acetyl-2',2'-dimethylcyclobutyl)acetic acid (473-72-3,17879-35-5,61376-92-9,61826-55-9,64396-97-0,127062-09-3,52305-34-7)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 6h;

DOI:10.1007/s11172-019-2575-3

Reference yield: 83.0%

Pinene (80-56-8,177698-18-9,25766-18-1) → (1'R,3'R)-2-(3'-acetyl-2',2'-dimethylcyclobutyl)acetic acid (473-72-3,17879-35-5,61376-92-9,61826-55-9,64396-97-0,127062-09-3,52305-34-7)

Guidance literature:

Pinene; With ozone; In dichloromethane; acetic acid; at 0 ℃;

With semicarbazide hydrochloride; In dichloromethane; acetic acid; at 0 - 20 ℃;

DOI:10.1134/S1070428014080016

upstream raw materials:

pinocamphone

rac-α-pinene

(3-acetyl-2,2-dimethylcyclobutyl)acetaldehyde

(+)-α-pinene

Downstream raw materials:

((1S)-2.2-dimethyl-3t-acetohydroximoyl-cyclobutyl-(r))-acetic acid

2,2-dimethyl-3-ethylcyclobutaneacetic acid

(+/-)-(3c-amino-2,2-dimethyl-cyclobut-r-yl)-acetic acid

trans-(2,2-dimethyl-3-acetylcyclobutyl)acetic acid

Refernces

• 1、 Garifullina, L. R.,Ishmuratov, G. Yu.,Myasoedova, Yu. V.,Nurieva, E. R.. "Transformations of Peroxide Ozonolysis Products of (–)-α-Pinene and (+)-3-Carene by the Action of 4-Hydroxybenzohydrazide". . p. 1673 - 1676. Retrieved 2020/10/22.
• 2、 Yakovleva,Mingaleeva,Denisova,Ishmuratov, G. Yu.. "Synthesis of optically active macrolides bearing di- and triethylene glycol and dicarboxylic acid hydrazide moieties from (-)-α-pinene". . p. 1445 - 1450. Retrieved 2019/08/12.