106-25-2 Usage
Identification test
Determination of total alcohol (OT-5). The amount of sample taken is 1.2g; the equivalent factor (e) in the calculation is 77.13.
Chemical properties
Colorless oily liquid It bears a sweet smell similar to the fresh rose, better than geraniol, and with hints of lemon flavor. The boiling point is 227 ℃; flash point is 92 ℃; optical rotation is [α] D ± 0 °. Miscible in ethanol, chloroform and ether; nearly insoluble in water.
It is the isomer of geraniol (trans; geraniol is cis).
Natural lanolin and its esters are found in orange leaf oil, rose oil, lavender oil, Sri Lanka citronella oil, bitter orange blossom oil and bergamot, lemon, white lemon, grapefruit, sweet orange and so on.
Uses
Different sources of media describe the Uses of 106-25-2 differently. You can refer to the following data:
1. The food flavors are mainly for the preparation of raspberry, strawberry and citrus fruit flavors and preparation of orange blossom, rose, magnolia main spices. It is a spice commonly used in jasmine, white flowers, lilac, lily of the valley, narcissus, carnation, mimosa, violet, vanilla, cymbidium, tuberose and citrus cologne. It is also commonly used in hyacinth, gardenia, osmanthus, acacia flavor formula. In the food flavor, its raspberry-strawberry flavor effect is commonly used. The product is also used in the preparation of daily makeup fragrance, such as violet, orange blossom, jasmine, lily of the valley, magnolia, cloves and other fragrance type makeup fragrance. It is widely used in orange blossom, rose, jasmine, tuberose and other fragrances of fragrant type and food flavor of raspberry, strawberry. It can also be used to produce ester spices.
2. Nerol is a flavoring agent that is a colorless liquid with an odor resem-
bling fresh, sweet roses and contains geranoils and other terpenic
alcohols. it is miscible in alcohol, chloroform, and ether insoluble
in water. it is obtained by synthesis. it is also termed cis-3,7-dime-
thyl-2,6-octadien-1-ol.
3. Nerol is an isomer of Geraniol (G367000), used in the synthesis of insect repellant. It is also used in the synthesis of Angelicoin A and Herecinone J, which inhibit collagen-induced platelet aggregat
ion.
4. nerol is a primary alcohol used in perfumes, especially those with rose and orange blossom scents. nerol is a naturally occurring fraction in oil of lavender, orange leaf, palmarosa, rose, neroli, and petitgrain. It is colorless and has a rose-like scent.
Preparation
Different sources of media describe the Preparation of 106-25-2 differently. You can refer to the following data:
1. 1. Oil of petitgrain is used as raw material; the first step is eliminating linalool and terpenes through fractionation; through saponification the fraction containing primary alcohol will be made into phthalate esters; and then going through purification and alkali saponification, geraniol (60 %) and nerol (40%) mixture is derived; removing geraniol with lead chloride, undergoing the residue vacuum distillation or steam distillation, the product was derived.
2. Let the geraniol and hydroiodic acid reacted in the neutral solution. Removing excess hydrogen iodide with alkali, the nerol mixed with geraniol can be derived, and then separate the mixture using the above method.
3. Heat the mixture of the same amount of camphor and acetic anhydride to boiling in the presence of sodium acetate. The mixture of geraniol and neryl alcohol can be derived through saponified esterification, and then separate the mixture by the former method.
4. Reducing citral in the isopropanol solution containing isopropanol aluminium also can obtain the mixture of geraniol and nerol, and nerol is derived through re-separation.
2. From pinene.
Toxicity
GRAS (FEMA).
LD504500 mg/kg (rat, oral).
maximum level?? ?FEMA (mg/kg): soft drink 1.4; cold drink 3.9; candy 16; baked food 19; pudding 1.0 to 1.3;
utilization limitation (FDA $ 172. 515, 2000).
Description
Nerol has a fresh, sweet, rose-like odor and a bitter flavor. Nerol may be synthesized from pinene.
Chemical Properties
Different sources of media describe the Chemical Properties of 106-25-2 differently. You can refer to the following data:
1. Nerol has a fresh, sweet, rose-like odor and a bitter flavor.
2. Clear colorless to almost colorless liquid
3. Nerol occurs in small
quantities in many essential oils where it is always accompanied by geraniol; its
name originates from its occurrence in neroli oil. Nerol is a colorless liquid with a
pleasant rose-like odor, which, unlike that of geraniol, has a fresh green note.
Nerol undergoes the same reactions as geraniol but cyclizes more readily in the
presence of acids.
Nerol is produced along with geraniol from myrcene in the process described
for geraniol. It can be separated from geraniol by fractional distillation.
Nerol is used in perfumery not only for the same purposes as geraniol,
for example, in rose compositions, to which it lends a particular freshness, but
also in other blossom compositions. In flavor work, it is used for bouquetting citrus
flavors. Technical-grade nerol, often in a mixture with geraniol, is used as an
intermediate in the production of citronellol and citral.
Occurrence
Reported found in neroli oil (with geraniol) and in the essential oils of lemongrass, Ceylon citronella, ylangylang, champaca, Cayenne Bois de Rose and bergamot; also in lemon, sweet orange and petitgrain bergamot; in clary sage, lavandin,
lavender, Mexican linaloe, myrrh, jasmine, Paraguay petitgrain; also reported among the volatile constituents of currant aroma;
Helicrysum angustifolium contains up to 30 to 50% nerol. Also reported found in citrus peel oils and juices, apricot, cranberry,
blueberry, currant, grapes, papaya, raspberry, blackberry, strawberry, potato, tomato, cinnamon, ginger, mentha oils, mustard, nutmeg, thyme, hop oil, beer, gin, cognac, brandy, grape wines, tea, honey, Arctic bramble, passion fruit, prune, Japanese plum, rose
apple, marjoram, mango, tamarind, cardamom, coriander seed and leaf, tarragon, litchi, licorice, buckwheat, laurel, wort, elderberry,
cherimoya, myrtle leaf and berry, buchu oil, Bourbon vanilla, lemon balm, clary sage, loganberry, maté, German chamomile oil and
mastic gum leaf oil.
Definition
ChEBI: The (2Z)-stereoisomer of 3,7-dimethylocta-2,6-dien-1-ol. It has been isolated from the essential oils from plants like lemon grass.
Aroma threshold values
Detection: 680 ppb to 2.2 ppm; aroma characteristics at 2%: rosy, slightly citrus, terpy and floral, reminiscent of linalool oxide with aldehydic waxy and fruity nuances
Taste threshold values
Taste characteristics at 10 ppm in 5% sugar and 0.1% CA: rosy with citrus nuances, fruity pear with floral
citronellal notes
Synthesis Reference(s)
Tetrahedron, 40, p. 641, 1984 DOI: 10.1016/S0040-4020(01)91092-0Tetrahedron Letters, 33, p. 5417, 1992 DOI: 10.1016/S0040-4039(00)79109-XSynthesis, p. 328, 1988 DOI: 10.1055/s-1988-27559
General Description
The antifungal efficacy of nerol (cis-3,7-Dimethyl-2,6-octadien-1-ol), against Aspergillus flavus, was studied.
Safety Profile
Moderately toxic by
intramuscular route. Mildly toxic by
ingestion. A skin irritant. When heated to
decomposition it emits acrid smoke and
irritating fumes.
Check Digit Verification of cas no
The CAS Registry Mumber 106-25-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 6 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 106-25:
(5*1)+(4*0)+(3*6)+(2*2)+(1*5)=32
32 % 10 = 2
So 106-25-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7-
106-25-2Relevant articles and documents
Selective Reduction of C=O in α,β-Unsaturated Carbonyls through Catalytic Hydrogen Transfer Reaction over Mixed Metal Oxides
Sonavane, Sachin U.,Jayaram, Radha V.
, p. 146 - 148 (2004)
Selective reduction of α,β-unsaturated carbonyls was studied over CoO-ZrO2 using propan-2-ol as a hydrogen donor and KOH as promoter in a liquid phase reaction. The catalyst used for this synthetically useful transformation showed considerable level of reusability as well as good activity.
A NOVEL REDUCING AGENT DERIVED FROM FORMIC ACID AND TWO EQUIVALENTS OF A GRIGNARD REAGENT: CHEMOSELECTIVE REDUCTION OF ALDEHYDES
Babler, James H.,Invergo, Benedict J.
, p. 621 - 622 (1981)
Aldehydes are reduced at a moderate rate by use of a novel reagent obtained by the addition of two molar eqivalents of ethylmagnesium bromide to formic acid in tetrahydrofuran solution.Under similar conditions the reduction of ketones proceeds quite slowly.
Regioselective 1,2-Reduction of Conjugated Enones and Enals with Sodium Monoacetoxyborohydride: Preparation of Allylic Alcohols
Nutaitis, Charles F.,Bernardo, Joseph E.
, p. 5629 - 5630 (1989)
-
Ni- and pd-catalyzed synthesis of substituted and functionalized allylic boronates
Zhang, Ping,Roundtree, Ian A.,Morken, James P.
, p. 1416 - 1419 (2012)
Two highly efficient and convenient methods for the synthesis of functionalized and substituted allylic boronates are described. In one procedure, readily available allylic acetates are converted to allylic boronates catalyzed by Ni/PCy3 or Ni/PPh3 complexes with high levels of stereoselectivity and in good yields. Alternatively, the borylation can be accomplished with commercially available Pd catalysts [e.g., Pd 2(dba)3, PdCl2, Pd/C], starting with easily accessed allylic halides.
FOUR ALIPHATIC ESTERS OF CHAMAEMELUM FUSCATUM ESSENTIAL OILY
Pascual-T., J. De,Caballero, E.,Caballero, C.,Anaya, J.,Gonzalez, M. S.
, p. 1757 - 1760 (1983)
Four new aliphatic esters were isolated from the essential oil of Chamaemelum fuscatum.Three are esters of methacrylicacid with 2-methyl-2E-butenol, 2-hydroxy-2-methyl-3-butenol and 2-hydroxy-2-methyl-3-oxobutanol.The other is neryl isovalerate obtained in addition to known compounds.The structures were determined by spectral measurements and by synthesis.Key Word Index-Chamaemelum fuscatum; Compositae; essential oil; aliphatic esters.
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Takabe,K. et al.
, p. 1031 - 1032 (1975)
-
A Bifunctional Copper Catalyst Enables Ester Reduction with H2: Expanding the Reactivity Space of Nucleophilic Copper Hydrides
Kaicharla, Trinadh,Ngoc, Trung Tran,Teichert, Johannes F.,Tzaras, Dimitrios-Ioannis,Zimmermann, Birte M.
supporting information, p. 16865 - 16873 (2021/10/20)
Employing a bifunctional catalyst based on a copper(I)/NHC complex and a guanidine organocatalyst, catalytic ester reductions to alcohols with H2 as terminal reducing agent are facilitated. The approach taken here enables the simultaneous activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H2, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guanidinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered "soft"copper(I) hydrides to previously unreactive "hard"ester electrophiles and paves the way for a replacement of stoichiometric reducing agents by a catalyst and H2.
Metal-doped mesoporous ZrO2catalyzed chemoselective synthesis of allylic alcohols from Meerwein-Ponndorf-Verley reduction of α,β-unsaturated aldehydes
Akinnawo, Christianah Aarinola,Bingwa, Ndzondelelo,Meijboom, Reinout
, p. 7878 - 7892 (2021/05/13)
Meerwein-Ponndorf-Verley reduction (MPVr) is a sustainable route for the chemoselective transformation of α,β-unsaturated aldehydes. However, tailoring ZrO2 catalysts for improved surface-active sites and maximum performance in the MPV reaction is still a challenge. Here, we synthesized mesoporous zirconia (ZrO2) and metal-doped zirconia (M_ZrO2, M = Cr, Mn, Fe, and Ni). The incorporation of metal dopants into zirconia's crystal framework alters its physico-chemical properties such as surface area and total acidity-basicity. The prepared catalysts were evaluated in the MPVr using 2-propanol as a hydrogen donor under mild reaction conditions. The catalysts' remarkable reactivity depends mainly on their surface mesostructure's intrinsic properties rather than the specific surface area. Cr_ZrO2, which is stable and sustainable, presented superior activity and 100% selectivity to unsaturated alcohols. The synergistic effect between Cr and Zr species in the binary oxide facilitated the Lewis acidity-induced performance of the Cr_ZrO2 catalyst. Our work presents the first innovative application of a well-designed mesoporous Cr_ZrO2 in the green synthesis of unsaturated alcohols with exceptional reactivity. This journal is
Hydroxypyridine ligand and preparation method and catalytic application thereof (by machine translation)
-
Paragraph 0086-0088, (2020/05/11)
The invention provides a hydroxypyridine ligand, a preparation method thereof and application, for catalyzing allyl alcohol isomerism, wherein the structural formula of the hydroxypyridine ligand is as follows : One or more, R wherein, R represents the substituent C1 - C20 selected from, alkyl, phenyl, naphthyl, heteroaryl, methoxy, fluoro, chloro, bromo, trifluoromethyl, methoxycarbonyl, amine has a higher catalytic activity, than that of a ligand 2 - such as an amine alcohol α, ω - hydroxyquinoline reported in the known literature and having a double-tooth chelating effect, and a metal tungsten bonding capability. The present invention provides, a; ligand 1,3 - and a, dihalide coupling, which can be rapidly, efficiently obtained . The, ligand has, a higher catalytic activity than the, metal tungsten bonding capability. (by machine translation)
