127-91-3 Usage
Description
Beta-pinene is a component of turpentine. Concentrations
vary depending on the source and seem to be
high er in European (Portuguese) than in Asian (Indonesian)
turpentines.
Chemical Properties
Different sources of media describe the Chemical Properties of 127-91-3 differently. You can refer to the following data:
1. liquid
2. β-Pinene occurs
in many essential oils. Optically active and racemic β-pinenes are present
in turpentine oils, although in smaller quantities than αα-pinene. (+)-β-Pinene,
(1R,5R)-6,6-dimethyl-2-methylenebicyclo(3.1.1)heptane,; (?)-β-Pinene, (1S,5S)-6,6-dimethyl-2-methylenebicyclo(3.1.1)heptane,.
β-Pinene is similar to α-pinene in its reactions. Pyrolytic cleavage to myrcene,
the startingmaterial for acyclic terpenes, is used on an industrial scale.Addition of
formaldehyde results in the formation of nopol; nopyl acetate is used as a fragrance
material. β-Pinene is produced in large quantities by distillation of turpentine oils.
It is used as a fragrance material in household perfumery.However,most β-pinene
is used in the production of myrcene.
3. β-Pinene has a characteristic turpentine odor with a dry, woody or resinous aroma.
Occurrence
Usually occurring together with α-pinene but in smaller amounts; the d- and l-forms are reported found in the
essential oils of various Artemisae and several Cupressaceae, in coriander and cumin; the l-form is a constituent of several citrus
oils. β-Pinene is reported found in over 190 natural products including apple, apricot, many citrus juices and peel oils, bilberry, cranberry,
lingonberry, blackberry, currants, guava, raspberry, strawberry, basil, carrot, celery, cooked potato, bell pepper, tomato, anise
seed oil, cinnamon, cassia leaf, clove, cumin, ginger, Mentha oils, nutmeg, mace, pepper, parsley, thyme, Swiss and cheddar cheese,
cream, fatty fish, fried chicken, beef fat, hop oil, rum, bourbon whiskey, tea, roasted filberts, pecans, oats, soybean, plum, mushroom,
sweet and wild marjoram, starfruit, mango, tamarind, cardamom, coriander, gin, rice, litchi, calamus, dill, lovage, caraway seed,
buckwheat, laurel, fennel, kiwifruit, myrtle leaf and berry, rosemary, buchu oil, Bourbon vanilla, Spanish and clary sage, nectarine,
crayfish, clam, cape gooseberry, anise hyssop, angelica root oil, Roman and German chamomile oil, eucalyptus oil, bullock’s heart
and mastic gum leaf and fruit oil.
Preparation
Isolated from American turpentine; also by conversion from α-pinene; as an intermediate extremely important for the
manufacture of citral, citronellol, hydroxycitronellal, geraniol, citronellal, linalool, ionones, methylionones and menthol.
Definition
ChEBI: An isomer of pinene with an exocyclic double bond. It is a component of essential oils from many plants.
Aroma threshold values
Detection: 140 ppb. Aroma characteristics at 10%: cooling, woody, piney and turpentine-like with a fresh
minty, eucalyptus and camphoraceous note with a spicy peppery and nutmeg nuance.
Taste threshold values
Taste characteristics at 15 to 100 ppm: fresh, piney and woody, terpy and resinous with a slight minty, spicy
and camphoraceous nuance.
Contact allergens
Beta-pinene is a component of turpentine. Concentrations
vary with the source and seem higher in
European (Portuguese) than in Asian (Indonesian)
turpentine.
Safety Profile
Mddly toxic by ingestion. A skin irritant. Flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 127-91-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 7 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 127-91:
(5*1)+(4*2)+(3*7)+(2*9)+(1*1)=53
53 % 10 = 3
So 127-91-3 is a valid CAS Registry Number.
InChI:InChI=1/C10H16/c1-7-4-5-8-6-9(7)10(8,2)3/h8-9H,1,4-6H2,2-3H3/t8-,9-/m1/s1
127-91-3Relevant articles and documents
A Convenient Synthesis of (+)-β-Pinene from (+)-α-Pinene
Harwood, Laurence M.,Julia, Marc
, p. 456 - 457 (1980)
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Hydroboration of Terpenes. 9. A Simple Improved Procedure for Upgrading the Optical Purity of Commercially Available α- and β-Pinenes. Conversion of (+)-α-Pinene to (+)-β-Pinene via Hydroboration-Isomerisation.
Brown, Herbert C.,Joshi, Nawalkishore N.
, p. 4059 - 4062 (1988)
An improved method for the preparation of optically pure diisopinocampheylborane (Ipc2BH) from commercially available (+)- and (-)-α-pinene (91-92percent ee) is described.The procedure, which is based on selective incorporation of the major enantiomer of α-pinene in crystalline dialkylborane, is both simple and efficient.Treatment with benzaldehyde liberates the parent olefin in very high enantiomeric excess (>99.5percent).The intermediate Ipc2BH can be thermally isomerized (130 deg C, 12h) to dimyrtanylborane, which is readily converted into the otherwise inaccessible (+)-β-pinene (>99.5) percent ee).In the course of this study it was established that the optical purification of commercial (-)-β-pinene too can be easily achieved by the formation and recrystallisation of tri-cis-myrtanylborane.Thus, simple manipulations via hydroboration provide easy access to all four enantiomers of α- and β-pinenes in very high optical purity.
Contra-thermodynamic Olefin Isomerization by Chain-Walking Hydroboration and Dehydroboration
Bloomer, Brandon,Butcher, Trevor W.,Ciccia, Nicodemo R.,Conk, Richard J.,Hanna, Steven,Hartwig, John F.
supporting information, p. 1005 - 1010 (2022/02/10)
We report a dehydroboration process that can be coupled with chain-walking hydroboration to create a one-pot, contra-thermodynamic, short-or long-range isomerization of internal olefins to terminal olefins. This dehydroboration occurs by a sequence comprising activation with a nucleophile, iodination, and base-promoted elimination. The isomerization proceeds at room temperature without the need for a fluoride base, and the substrate scope of this isomerization is expanded over those of previous isomerizations we have reported with silanes.
Oxidation of α-pinene by atmospheric oxygen in the supercritical CO2-ethyl acetate system in the presence of Co(II) complexes
Anikeev,Ilina,Kurbakova,Nefedov,Volcho,Salakhutdinov
experimental part, p. 190 - 195 (2012/03/12)
The reactivity of monoterpene α-pinene in a flow reactor in the presence of cobalt catalyst in a complex supercritical solvent consisting of CO2 and ethyl acetate is studied over the temperature range of 190-320°C and a pressure range of 110-125 atm. It was found that the main isomerization products include compounds with bicyclo[2.2.1]heptane and p-menthane backbones; the reaction is accompanied by partial racemization. The formation of oxidation products is observed in the presence of air, with epoxydation rather than allylic oxidation being the predominant process at the first stage. The oxidized products (campholenic aldehyde, verbenone, pinocamphone) are shown to be formed with a high enantioselectivity; the formation of acetoxylation products is observed at temperatures above 200°C.
ORALLY EFFECTIVE CANNABINOID ANALOGS
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Page/Page column 33-35, (2008/06/13)
The present invention relates to orally effective ligands of the peripheral cannabinoid thereof, receptor CB2 especially (+)-α pinene derivatives, and to pharmaceutical compositions thereof, which are useful for prevention, alleviation or treatment of autoimmune neurodegenerative disorders, in particular multiple sclerosis and associated symptoms. Methods of the invention are useful when the active ingredient is administered alone or in combination with existing therapeutic modalities. The compositions are administered by oral route.
