106-25-2 Usage
Description
2,6-Octadien-1-ol,3,7-dimethyl-, (2Z)-, also known as Nerol, is a colorless liquid with a fresh, sweet, rose-like odor and a bitter flavor. It is an isomer of Geraniol and is commonly found in essential oils from plants like lemon grass. Nerol can be synthesized from pinene and is produced along with geraniol from myrcene. It undergoes the same reactions as geraniol but cyclizes more readily in the presence of acids. Nerol is used in perfumery 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.
Uses
Used in Flavor Industry:
2,6-Octadien-1-ol,3,7-dimethyl-, (2Z)is used as a flavoring agent for its raspberry-strawberry flavor effect in the preparation of raspberry, strawberry, and citrus fruit flavors. It is also used in the preparation of orange blossom, rose, magnolia main spices, and 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.
Used in Perfumery:
2,6-Octadien-1-ol,3,7-dimethyl-, (2Z)is used as a primary alcohol in perfumes, especially those with rose and orange blossom scents. It is a naturally occurring fraction in oil of lavender, orange leaf, palmarosa, rose, neroli, and petitgrain.
Used in Synthesis of Insect Repellent:
2,6-Octadien-1-ol,3,7-dimethyl-, (2Z)is used in the synthesis of insect repellant and is also used in the synthesis of Angelicoin A and Herecinone J, which inhibit collagen-induced platelet aggregation.
Used in Antifungal Applications:
The antifungal efficacy of nerol (cis-3,7-Dimethyl-2,6-octadien-1-ol), against Aspergillus flavus, has been studied.
Used in Production of Ester Spices:
2,6-Octadien-1-ol,3,7-dimethyl-, (2Z)can also be used to produce ester spices.
Occurrence:
2,6-Octadien-1-ol,3,7-dimethyl-, (2Z)has been reported found in neroli oil (with geraniol) and in the essential oils of lemongrass, Ceylon citronella, ylang-ylang, champaca, Cayenne Bois de Rose, and bergamot. It is also found 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. It is 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.
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.
Preparation
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.
Preparation
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).
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
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)
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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)
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Method for preparing nerol from geraniol
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Paragraph 0046-0047, (2021/01/25)
The invention provides a method for preparing nerol from geraniol. According to the method, calix[4] aryl zinc compound catalysts are used for catalyzing geraniol to be converted into nerol. The method is especially suitable for converting a natural or artificially synthesized mixture of nerol and geraniol in any proportion into nerol.
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.
Hydroxypyridine ligand and preparation method and catalytic application thereof (by machine translation)
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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)