38630-75-0

Basic information

• Product Name: (+)-(1S,2S,4R)-Limonene glycol, (+)-1-Hydroxyneodihydrocarveol, (1S,2S,4R)-(+)-p-Menth-8-en-1,2-diol, (1S,2S,4R)-(+)-4-Isopropenyl-1-methylcyclohexan-1,2-diol, (1S,2S,4R)-8-p-Menth-8-ene-1,2-diol
• Synonyms: (+)-(1S,2S,4R)-Limonene glycol, (+)-1-Hydroxyneodihydrocarveol, (1S,2S,4R)-(+)-p-Menth-8-en-1,2-diol, (1S,2S,4R)-(+)-4-Isopropenyl-1-methylcyclohexan-1,2-diol, (1S,2S,4R)-8-p-Menth-8-ene-1,2-diol;(1S,2S,4R)-(+)-Limonene-1,2-diol;(+)-(1S,2S,4R)-Limonene glycol
• CAS NO: 38630-75-0
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.25
• Mol File: 38630-75-0.mol

Chemical Properties

• Melting Point: 68-72 °C
• Boiling Point: 241.7±40.0 °C(Predicted)
• Appearance: /
• Density: 1.035±0.06 g/cm3(Predicted)
• PKA: 14.69±0.60(Predicted)
• BRN: 2325340
• CAS DataBase Reference: (+)-(1S,2S,4R)-Limonene glycol, (+)-1-Hydroxyneodihydrocarveol, (1S,2S,4R)-(+)-p-Menth-8-en-1,2-diol, (1S,2S,4R)-(+)-4-Isopropenyl-1-methylcyclohexan-1,2-diol, (1S,2S,4R)-8-p-Menth-8-ene-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(1S,2S,4R)-Limonene glycol, (+)-1-Hydroxyneodihydrocarveol, (1S,2S,4R)-(+)-p-Menth-8-en-1,2-diol, (1S,2S,4R)-(+)-4-Isopropenyl-1-methylcyclohexan-1,2-diol, (1S,2S,4R)-8-p-Menth-8-ene-1,2-diol(38630-75-0)
• EPA Substance Registry System: (+)-(1S,2S,4R)-Limonene glycol, (+)-1-Hydroxyneodihydrocarveol, (1S,2S,4R)-(+)-p-Menth-8-en-1,2-diol, (1S,2S,4R)-(+)-4-Isopropenyl-1-methylcyclohexan-1,2-diol, (1S,2S,4R)-8-p-Menth-8-ene-1,2-diol(38630-75-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 38630-75-0(Hazardous Substances Data)

Usage

Uses

Used in Synthesis of Natural Products and Pharmaceuticals:
(+)-(1S,2S,4R)-Limonene glycol, (+)-1-Hydroxyneodihydrocarveol, (1S,2S,4R)-(+)-p-Menth-8-en-1,2-diol, (1S,2S,4R)-(+)-4-Isopropenyl-1-methylcyclohexan-1,2-diol, and (1S,2S,4R)-8-p-Menth-8-ene-1,2-diol are used as chiral building blocks for the synthesis of various natural products and pharmaceuticals. Their unique stereochemistry and functional groups enable the development of enantioselective synthetic routes, leading to the production of biologically active compounds with potential applications in medicine, agriculture, and fragrance industries.
Used in Flavor and Fragrance Industry:
(+)-(1S,2S,4R)-Limonene glycol, (+)-1-Hydroxyneodihydrocarveol, (1S,2S,4R)-(+)-p-Menth-8-en-1,2-diol, (1S,2S,4R)-(+)-4-Isopropenyl-1-methylcyclohexan-1,2-diol, and (1S,2S,4R)-8-p-Menth-8-ene-1,2-diol are used as key intermediates in the synthesis of flavor and fragrance compounds. Their unique olfactory properties and chiral characteristics make them valuable components in the creation of new and improved fragrances, as well as in the development of novel taste modifiers for the food industry.
Used in Agrochemicals:
(+)-(1S,2S,4R)-Limonene glycol, (+)-1-Hydroxyneodihydrocarveol, (1S,2S,4R)-(+)-p-Menth-8-en-1,2-diol, (1S,2S,4R)-(+)-4-Isopropenyl-1-methylcyclohexan-1,2-diol, and (1S,2S,4R)-8-p-Menth-8-ene-1,2-diol are used as precursors in the synthesis of agrochemicals, such as insecticides, herbicides, and plant growth regulators. Their chiral nature allows for the development of enantioselective pesticides with improved efficacy and reduced environmental impact.
Used in Materials Science:
(+)-(1S,2S,4R)-Limonene glycol, (+)-1-Hydroxyneodihydrocarveol, (1S,2S,4R)-(+)-p-Menth-8-en-1,2-diol, (1S,2S,4R)-(+)-4-Isopropenyl-1-methylcyclohexan-1,2-diol, and (1S,2S,4R)-8-p-Menth-8-ene-1,2-diol are used as monomers in the synthesis of chiral polymers and materials with unique properties, such as self-assembly, optical activity, and stimuli-responsive behavior. These materials have potential applications in various fields, including sensors, drug delivery systems, and nanotechnology.

Upstream product

• 5989-27-5 D-limonene 
• 1195-92-2 (4R)-limonene 1,2-epoxide 
• 1195-92-2 Limonene oxide 
• 4680-24-4 cis-(R)-limonene oxide 
• 6909-30-4 (1S,2R,4R)-limonene-1,2-epoxide 
• 58506-22-2 p-menthane-1,2,8-triol 
• 7722-84-1 dihydrogen peroxide 
• 64-19-7 acetic acid 
• 138-86-3 limonene. 
• 5989-54-8 (-)-(S)-limonene 
• 15249-34-0 Linalool oxide 
• 203719-54-4 (1RS,2SR,4R)-limonene-1,2-epoxide 
• 29428-57-7 threo-1,2-epoxy-3,7-dimethy-6-octen-3-ol 
• 15249-34-0 1,2-epoxylinalool 

Downstream Products

• 23733-68-8 p-menth-3-en-2-one 
• 4031-57-6 (1S,2S,4R)-4-isopropyl-1-methylcyclohexane-1,2-diol 
• 5745-59-5 (-)-1-hydroxyneoisocarvomenthol 
• 6909-26-8 (+)-1-Hydroxy-neodihydrocarveyl-tosylat 
• 62014-81-7 (1S,2S,4R)-p-menthane-1,2,8-triol 
• 5206-83-7 (1R,4R)-(+)-carvomenthone 
• 18383-51-2 (-)-trans-carveol 
• 33669-76-0 p-menthane-1,2-diol 
• 4031-57-6 (1RS,2SR,4RS)-p-menthane-1,2-diol 
• 5581-31-7 4-(1,2-dihydroxypropan-2-yl)-1-methylcyclohexane-1,2-diol 
• 7105-59-1 3-Isopropenyl-6-oxo-heptansaeure-methylester 
• 499-70-7 carvomenthone 
• 7086-80-8 2-hydroxy-5-isopropenyl-2-methylcyclohexanone 
• 24047-73-2 (2S,5R)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexanone 

Relevant articles and documents

A silicododecamolybdate/pyridinium-tetrazole hybrid molecular salt as a catalyst for the epoxidation of bio-derived olefins

The hybrid polyoxometalate (POM) salt (Hptz)4[SiMo12O40]?nH2O (1) (ptz = 5-(2-pyridyl)tetrazole) has been prepared, characterized by X-ray crystallography, and examined as a catalyst for the epoxidation of cis-cyclooctene (Cy) and bio-derived olefins, namely dl-limonene (Lim; a naturally occurring monoterpene found in the rinds of citrus fruits), methyl oleate and methyl linoleate (fatty acid methyl esters (FAMEs) obtained by transesterification of vegetable oils). The crystal structure of 1 consists of α-Keggin-type heteropolyanions, [SiMo12O40]4-, surrounded by space-filling and charge-balancing 2-(tetrazol-5-yl)pyridinium (Hptz+) cations, as well as by a large number of water molecules of crystallization (n = 9). The water molecules mediate an extensive three-dimensional (3D) hydrogen-bonding network involving the inorganic anions and organic cations. For the epoxidation of the model substrate Cy in a nonaqueous system (tert-butylhydroperoxide as oxidant), the catalytic performance of 1 (100% epoxide yield at 24 h, 70 °C) was superior to that of the tetrabutylammonium salt (Bu4N)4[SiMo12O40] (2) (63% epoxide yield at 24 h), illustrating the role of the counterion Hptz+ in enhancing catalytic activity. The hybrid salt 1 was effective for the epoxidation of Lim (69%/85% conversion at 6 h/24 h) and the FAMEs (87–88%/100% conversion at 6 h/24 h), leading to useful bio-based products (epoxides, diepoxides and diol products).

Selective Catalytic Synthesis of 1,2- and 8,9-Cyclic Limonene Carbonates as Versatile Building Blocks for Novel Hydroxyurethanes

The selective catalytic synthesis of limonene-derived monofunctional cyclic carbonates and their subsequent functionalisation via thiol–ene addition and amine ring-opening is reported. A phosphotungstate polyoxometalate catalyst used for limonene epoxidation in the 1,2-position is shown to also be active in cyclic carbonate synthesis, allowing a two-step, one-pot synthesis without intermittent epoxide isolation. When used in conjunction with a classical halide catalyst, the polyoxometalate increased the rate of carbonation in a synergistic double-activation of both substrates. The cis isomer is shown to be responsible for incomplete conversion and by-product formation in commercial mixtures of 1,2-limomene oxide. Carbonation of 8,9-limonene epoxide furnished the 8,9-limonene carbonate for the first time. Both cyclic carbonates underwent thiol–ene addition reactions to yield linked di-monocarbonates, which can be used in linear non-isocyanate polyurethanes synthesis, as shown by their facile ring-opening with N-hexylamine. Thus, the selective catalytic route to monofunctional limonene carbonates gives straightforward access to monomers for novel bio-based polymers.

Sustainable catalytic protocols for the solvent free epoxidation and: Anti -dihydroxylation of the alkene bonds of biorenewable terpene feedstocks using H2O2 as oxidant

A tungsten-based polyoxometalate catalyst employing aqueous H2O2 as a benign oxidant has been used for the solvent free catalytic epoxidation of the trisubstituted alkene bonds of a wide range of biorenewable terpene substrates. This epoxidation protocol has been scaled up to produce limonene oxide, 3-carene oxide and α-pinene oxide on a multigram scale, with the catalyst being recycled three times to produce 3-carene oxide. Epoxidation of the less reactive disubstituted alkene bonds of terpene substrates could be achieved by carrying out catalytic epoxidation reactions at 50 °C. Methods have been developed that enable direct epoxidation of untreated crude sulfate turpentine to afford 3-carene oxide, α-pinene oxide and β-pinene oxide. Treatment of crude epoxide products (no work-up) with a heterogeneous acid catalyst (Amberlyst-15) results in clean epoxide hydrolysis to afford their corresponding terpene-anti-diols in good yields.

Limonene oxyfunctionalization over Cu-modified silicates employing hydrogen peroxide and t-Butyl hydroperoxide: Reaction pathway analysis

Limonene oxidation over Cu-nanostructured mesoporous materials was studied. Three solids with different copper content were synthesized employing the template-ion exchange method, and physically-chemically analyzed by a multi-technical characterization. The performance of the molecular sieves as catalysts in the liquid phase oxyfunctionalization of limonene, employing hydrogen peroxide (H2O2) or t-butyl hydroperoxide (TBHP) as oxidants was evaluated. All synthesized Cu-MCM materials were active in the reaction. The obtained results showed that the used oxidant had an important influence on the products distribution under the employed conditions. With H2O2, compounds of high added value such as limonene oxide, carveol and carvone were mainly obtained. Meanwhile, with TBHP, limonene hydroperoxide turned out to be the major product. Finally, a reaction mechanism was proposed for each oxidant.

Systematic synthetic study of four diastereomerically distinct limonene-1,2-diols and their corresponding cyclic carbonates

In order to produce versatile and potentially functional terpene-based compounds, a (R)-limonene-derived diol and its corresponding five-membered cyclic carbonate were prepared. The diol (cyclic carbonate) comprises four diastereomers based on the stereochemical configuration of the diol (and cyclic carbonate) moiety. By choosing the appropriate starting compounds (trans- and cis-limonene oxide) and conditions, the desired diastereomers were synthesised in moderate to high yields with, in most cases, high stereoselectivity. Comparison of the NMR data of the obtained diols and carbonates revealed that the four different diastereomers of each compound could be distinguished by reference to their characteristic signals.

Oxy-functionalization of olefins with neat and heterogenized binuclear V(IV)O and Fe(II)complexes: Effect of steric hindrance on product selectivity and output in homogeneous and heterogeneous phase

Neat {[VO(sal2bz)]2; [Fe(sal2bz)(H2O)2]2·2H2O} and zeolite-Y immobilized {[VO(sal2bz)]2-Y; [Fe(sal2bz)(H2O)2]2-Y} binuclear complexes have been prepared and characterized by spectroscopic techniques (IR, UV–vis), elemental analyses (CHN, ICP-OES), thermal study (TGA), scanning electron micrograph (SEM), adsorption study (BET)and X-ray diffraction (XRD)patterns. Neat (homogeneous)and immobilized (heterogeneous)complexes were employed as catalysts in the oxidation of olefins, namely, cyclohexene, limonene and α-pinene in the presence of 30% hydrogen peroxide. 100% conversion of cyclohexene and α-pinene was obtained while limonene was oxidized up to 90%. Homogeneous catalysts showed highly selective result as neat [VO(sal2bz)]2 complex has provided 87% cyclohexane-1,2-diol and neat [Fe(sal2bz)(H2O)2]2·2H2O complex has provided 79% verbenone in oxidation of cyclohexene and α-pinene, respectively. We have observed that due to steric hindrance, formation of olefinic oxidation products increases on moving from α-pinene to limonene and limonene to cyclohexene. Additionally. recovered heterogeneous catalysts showed intact results up to two consecutive runs. Probable catalytic mechanism has been proposed for oxidation of cyclohexene.

Performance of chiral tetracarbonylmolybdenum pyrindanyl amine complexes in catalytic olefin epoxidation

Tetracarbonylmolybdenum(0) complexes of the type cis-[Mo(CO)4(L)] containing chiral 7-(1-pyrindanyl) amine ligands were prepared and found to be effective precatalysts for the epoxidation of achiral (cis-cyclooctene) and prochiral (DL-limonene and trans-β-methylstyrene) olefins at 55 °C. Epoxides were the only products formed from cis-cyclooctene (100% yield) and trans-β-methylstyrene (100% selectivity at 82–85% conversion), and the main products formed from DL-limonene (80–82% 1,2-epoxide selectivity at 85% conversion). Characterization of recovered catalysts revealed that the precatalysts were transformed in situ to stable polyoxomolybdate salts containing the β-octamolybdate anion [β-Mo8O26]4?, which was responsible for the catalytic reaction.

Kinetics of the Aqueous Phase Reactions of Atmospherically Relevant Monoterpene Epoxides

Laboratory and field measurements have demonstrated that an isoprene-derived epoxide intermediate (IEPOX) is the origin of a wide range of chemical species found in ambient secondary organic aerosol (SOA). In order to explore the potential relevance of a similar mechanism for the formation of monoterpene-derived SOA, nuclear magnetic resonance techniques were used to study kinetics and reaction products of the aqueous-phase reactions of several monoterpene epoxides: β-pinene oxide, limonene oxide, and limonene dioxide. The present results, combined with a previous study of α-pinene oxide, indicate that all of these epoxides will react more quickly than IEPOX with aqueous atmospheric particles, even under low-acidity conditions. As for α-pinene oxide, the observed products can be mainly rationalized with a hydrolysis mechanism, and no long-lived organosulfate or nitrate species nor species that retain the β-pinene bicyclic carbon backbone are observed. As bicyclic ring-retaining organosulfate and nitrate species have been previously observed in monoterpene-derived SOA, it appears that monoterpene-derived epoxides may not be as versatile as IEPOX in producing a range of SOA species, and other mechanisms are needed to rationalize organosulfate and nitrate formation.

Influence of ligand substitution on molybdenum catalysts with tridentate Schiff base ligands for the organic solvent-free oxidation of limonene using aqueous TBHP as oxidant

The oxidation of limonene by aqueous TBHP has been analyzed in the presence of molybdenum complexes [MoO2L]2 as catalysts with five different tridentate ligands L in the absence of organic solvents (greener reaction conditions). The ligands are based on a common salicylidene amino(thio)phenolate, SA(T)P, backbone with differences in the coordination sphere (ONO for L = SAP vs. ONS for L = SATP) or in the salicyl moiety functionalization by OH groups for the ONO ligands. The process gives a regioselective endocyclic epoxidation to a kinetically controlled 1:1 mixture of the cis-LimO and trans-LimO epoxides and/or the isomeric diols ax-LimD and eq-LimD by the subsequent ring opening in the presence of water, with a product distribution that depends on the ligand, reaction time and temperature. In combination with control experiments of the cis/trans-LimO ring opening, the investigations demonstrate the catalytic action of the metal complexes in both the epoxidation and the ring opening steps, with the cis-LimO stereospecifically producing the ax-LimD product and the less reactive trans-LimO leading to a 4:3 mixture of ax-LimD and eq-LimD. The ONS system [MoO2(SATP)]2 exhibits the highest catalytic activity in both steps.

Catalytic homogeneous oxidation of monoterpenes and cyclooctene with hydrogen peroxide in the presence of sandwich-type tungstophosphates [M4(H2O)2(PW9O34)2]n?, M = CoII, MnII and FeIII

Catalytic efficiency of tetrabutylammonium salts of sandwich tungstophosphates B‐α‐[M4(H2O)2(PW9O34)2]n?, M = CoII, MnII, FeIII, was studied in the oxidation of (R)-(+)-limonene, geraniol, linalool, linalyl acetate, carveol, and cis-cyclooctene with hydrogen peroxide, in acetonitrile. Oxidation of (R)-(+)-limonene gave limonene-1,2-diol as main product. Epoxidation of linalool takes place preferentially at the more substituted 6,7-double bond, the corresponding 6,7-epoxide reacting further, yielding furano- and pyrano-oxides, via intramolecular cyclization. Oxidation of linalyl acetate occurred preferentially at the more substituted 6,7-double bond for Mn4(PW9)2, affording 6,7-epoxide at 82% selectivity. Linalyl acetate 1,2-epoxide was the major product with 51% and 77% selectivity for Co4(PW9)2 and Fe4(PW9)2, respectively. Oxidation of carveol occurred with very good conversions in the presence of Mn4(PW9)2, Co4(PW9)2 and Fe4(PW9)2, yielding carvone and carveol 1,2-epoxide in similar amounts. Oxidation of cis-cyclooctene gave only the epoxide, while oxidation of geraniol at room temperature afforded 2,3-epoxygeraniol as the major product.