473-72-3

Usage

Uses

Used in Atmospheric Chemistry Research:
Pinonic Acid is used as a marker for atmospheric chemistry research, particularly in studying the formation and behavior of secondary organic aerosols (SOAs). Its low volatility allows it to contribute to the growth and lifetime of SOAs, which play a crucial role in climate regulation and air quality.
Used in Environmental Monitoring:
Pinonic Acid is used as an indicator for environmental monitoring, helping to assess the levels of air pollution and the presence of specific atmospheric radicals. Its detection can provide valuable insights into the chemical processes occurring in the atmosphere and the potential impacts on human health and the environment.
Used in Analytical Chemistry:
Pinonic Acid is used as an analytical standard in the development and calibration of analytical instruments, such as mass spectrometers and gas chromatographs. Its unique chemical properties make it a valuable reference compound for accurately measuring and identifying other atmospheric constituents.
Used in Air Quality Management:
Pinonic Acid is used in air quality management strategies to help develop effective measures for reducing emissions of volatile organic compounds (VOCs), such as α-pinene, which contribute to the formation of SOAs and poor air quality. Understanding the role of Pinonic Acid in atmospheric chemistry can inform the development of policies and technologies aimed at improving air quality and mitigating climate change.

InChI:InChI=1/C10H16O4/c1-6(11)14-8-4-7(5-9(12)13)10(8,2)3/h7-8H,4-5H2,1-3H3,(H,12,13)

Upstream product

• 18358-53-7 pinocamphone 
• 80-56-8 rac-α-pinene 
• 2704-78-1 (3-acetyl-2,2-dimethylcyclobutyl)acetaldehyde 
• 7785-70-8 (+)-α-pinene 
• 7722-84-1 dihydrogen peroxide 
• 75-65-0 tert-butyl alcohol 
• 7785-26-4 (-)-α-pinene 
• 74281-22-4 2-((1R,3R)-3-acetyl-2,2-dimethylcyclobutyl)acetaldehyde 
• 80-56-8 Pinene 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 28899-97-0 triphenylbismuth(V) diacetate 
• 18680-27-8 pinanediol 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 1845-25-6 (1S,2S,5S)-(-)-2-hydroxypinan-3-one 

Downstream Products

• 77370-41-3 3-methylbutane-1,2,3-tricarboxylic acid 
• 92223-72-8 hydroxy-trimethyl-succinic acid 
• 144-62-7 oxalic acid 
• 79-91-4 terebic acid 
• 2051-44-7 3-carboxymethyl-2,2-dimethyl-glutaric acid 
• 99974-72-8 3-(1,1-dimethyl-2-oxo-propyl)-glutaric acid 
• 64-19-7 acetic acid 
• 16978-11-3 pinonic acid methyl ester 
• 24903-95-5 nopinone 
• 28664-03-1 (3-ethoxycarbonyl-2,2-dimethyl-cyclobutyl)-acetic acid ethyl ester 
• 473-54-1 trans-2,6,6-trimethylbicyclo(3.1.1)-heptan-2-ol 
• 4436-81-1 homoterpenylmethylketone 
• 24894-10-8 (+)-[(1R)-3c-((Ξ)-1-hydroxy-ethyl)-2,2-dimethyl-cyclobut-r-yl]-acetic acid methyl ester 
• 2234-20-0 2,4-dimethylstyrene 

Relevant academic research and scientific papers

Molecular Chirality and Cloud Activation Potentials of Dimeric α-Pinene Oxidation Products

The surface activity of ten atmospherically relevant α-pinene-derived dimers having varying terminal functional groups and backbone stereochemistry is reported. We find ～10% differences in surface activity between diastereomers of the same dimer, demonstrating that surface activity depends upon backbone stereochemistry. Octanol-water (KOW) and octanol-ammonium sulfate partitioning coefficient (KOAS) measurements of our standards align well with the surface activity measurements, with the more surface-active dimers exhibiting increased hydrophobicity. Our findings establish a link between molecular chirality and cloud activation potential of secondary organic aerosol particles. Given the diurnal variations in enantiomeric excess of biogenic emissions, possible contributions of such a link to biosphere:atmosphere feedbacks as well as aerosol particle viscosity and phase separation are discussed.

Transformations of Peroxide Ozonolysis Products of (–)-α-Pinene and (+)-3-Carene by the Action of 4-Hydroxybenzohydrazide

Abstract: Treatment of peroxide ozonolysis products of the bicyclic monoterpenes (–)-α-pinene and (+)-3-carene with 4-hydroxybenzohydrazide in methylene chloride or tetrahydrofuran gave the corresponding keto acids, whereas keto esters were formed in methanol.

Synthesis of Isonicotinic and Salicylic Acids Derivatives from (–)-α-Pinene and (+)-Δ3-Carene

Abstract: Optically active cyclobutanediyl- and cyclopropanediylbisalkylidenedihydrazides of isonicotinic and salicylic acids were synthesized when theperoxide products of ozonolysis of (–)-α-pinene and(+)-Δ3-carene were reduced with isonicotin

Synthesis of optically active macrolides bearing di- and triethylene glycol and dicarboxylic acid hydrazide moieties from (-)-α-pinene

Six optically active macroheterocycles bearing ester and dihydrazide moieties were synthesized from available natural (-)-α-pinene through the intermediate keto acid, (31R,33R)- 1-hydroxy-32,32-dimethyl-1,4-dioxopentaphane, using the [2+1] reaction of this keto acid with di- or triethylene glycols and the [1+1] condensation of the resulting α,ω-diketo diesters with dicarboxylic acid dihydrazides in the key steps.

Transformations of (-)-α-pinene peroxide ozonolysis products by hydrazines of HCL and H2SO4

The reactivities of hydrazines of HCl and H2SO4 for (-)-α-pinene peroxide ozonolysis products were studied. It was shown that these reagents were less effective and selective than semicarbazide hydrochloride for transformations into cis-pinonic acid and its esters.

Transformations of peroxide products of olefin ozonolysis in tetrahydrofuran in reactions with hydroxylamine and semicarbazide hydrochlorides

Treatment with hydroxylamine and semicarbazide hydrochlorides of peroxide products obtained by ozonolysis of olefins in tetrahydrofuran gives mainly carboxylic acids and their derivatives.

Transformation of peroxide products of olefin ozonolysis under treatment with hydroxylamine and semicarbazide hydrochlorides in acetic acid

Hydrochlorides of hydroxylamine and semicarbazide efficiently reduce peroxide products of olefin ozonolysis in a system CH2Cl2-AcOH leading to the formation of carboxylic acids and their derivatives. The application of water as the solvent component favors the increase in the fraction of nitrogen-containing organic compounds (semicarbazones, keto- and aldoximes, nitriles) and reduction in the yield of carboxylic acids.

Tetrapropylammonium perruthenate catalyzed glycol cleavage to carboxylic (Di)acids

A new method to accomplish glycol cleavage to carboxylic (di)acids in one step using catalytic amounts of tetrapropylammonium perruthenate (TPAP) together with N-methylmorpholine N-Oxide (NMO) as the stoichiometric oxidant is presented. In addition to regenerating the active catalyst, the N-oxide stabilizes intermediary carbonyl hydrates and thereby shifts a crucial equilibrium. The mild oxidation protocol is applicable to a broad range of substrates providing the respective acids, diacids, or keto acids in high yields.

Efficient synthesis of chiral Δ2-1,3,4-thiadiazolines from α-pinene and verbenone

The synthesis of chiral cyclobutane 1,3,4-thiadiazoline derivatives starting from (-)-α-pinene and (-)-verbenone was studied. The diastereoisomeric excesses of the products obtained depended strongly upon the starting chiral ketone. The stereochemical assignments of the synthesized compounds were performed by NMR spectroscopy, X-ray analysis, and theoretical calculations.

2-Azapinanes: Aza Analogues of the Enantiomeric Pinyl Carbocation Intermediates in Pinene Biosynthesis

The enantiomeric 2-azapinanes, aza analogues of the pinyl carbocation intermediates in pinene biosynthesis, were synthesized from (-)-and (+)-cis-pinonic acids. The individual reactions in the 5-step sequence were Beckmann rearrangement of the pinonic acid oximes, cyclization to the N-acetyl lactams, hydrolysis to the NH-lactams, N-methylations, and LiAlH4 reductions. The anti stereochemistry of the N-methyl groups in the salts with respect to the gem-dimethyl bridge was established by NOE measurements and by X-ray diffraction analysis.(Figure Presented)