7212-44-4 Usage
Description
Different sources of media describe the Description of 7212-44-4 differently. You can refer to the following data:
1. Nerolidol occurs naturally including the essential oil of neroli, ylang-ylang, and Peru balsam. It has a faint, fresh, unusually sweet, tenacious, floral odor similar to rose and apple. It can be used as a flavor ingredient in foods, such as baked goods, frozen dairy, nonalcoholic beverages, and soft candy. It is also used as fragrance in the perfumery.
2. Nerolidol has a faint, floral odor similar to rose and apple. It is an unusually sweet, fresh, tenacious odor. The natural product can be dextro- or levo-rotatory, whereas the synthetic product is optically inactive; the double bond at positions 6-7 accounts for the cis- and trans-forms.
References
[1] George A. Burdock, Fenaroli's Handbook of Flavor Ingredients, 6th Edition, 2010
Chemical Properties
Different sources of media describe the Chemical Properties of 7212-44-4 differently. You can refer to the following data:
1. Nerolidol has a faint, fresh, unusually sweet, tenacious, floral odor similar to rose and appe
2. Clear slightly yellow liquid
3. Nerolidol is the sesquiterpene
analog of linalool. Because of the double bond at the 6-position, it exists as (6Z)- and (6E)- isomers, each forming an enantiomeric pair,
since the carbon atom in the 3-position is asymmetric.
Nerolidol is a component of many essential oils. (3S,6E)-(+)-nerolidol occurs in cabreuva oil.
Synthetic nerolidol consists of a mixture of racemic (6Z)- and (6E)-nerolidol
and is a colorless liquid with a long-lasting, mild floral odor.
Industrial synthesis of nerolidol starts with linalool, which is converted into
geranylacetone by using diketene, ethyl acetoacetate, or isopropenyl methyl
ether, analogously to the synthesis of 6-methyl-5-hepten-2-one from 2-methyl-
3-buten-2-ol. Addition of acetylene and partial hydrogenation of the resultant
dehydronerolidol produces a mixture of (6Z)- and (6E)-nerolidol racemates.Nerolidol is used as a base note in many delicate floral odor complexes. It is also
an intermediate in the production of vitamins E and K1.
Occurrence
Reported found in over 25 natural sources, including the essential oils of neroli, ylang-ylang, Peru balsam; in
currant aroma; also reported in Dalbergia sissoo (60%, dl-), vervain, the distillation water of petitgrain bigarade, Helicrysum italicum, Myrocarpus frondosus and Myrocarpus fastigiatus (80%, d-), Tolu balsam, Acacia farnesiana, orange flower water, Paraguay
petitgrain, jasmine, Melaleuca smithii and Melaleuca viridiflora. Also reported found in citrus peel oils and juices, guava, strawberry, peppermint and spearmint oil, pepper, milk powder, hop oil, beer, cognac, white wine, green tea, beans, mushroom, cardamom, rice, dill, corn oil, basil, wort, myrtle leaf, maté and mastic gum oil.
Uses
Different sources of media describe the Uses of 7212-44-4 differently. You can refer to the following data:
1. Nerolidol is one of the main component in the essential oils from fresh aerial parts of Thymus ciliatus (Lamiaceae). Also, it is a terpene that displays high potency on the contractility of cardiac muscle in guinea pig left atrium. A potential and effective treatment for malaria.
2. anti-ulcer, insect antifeedant
Aroma threshold values
Detection: 10 ppb to 10 ppm
Taste threshold values
Taste characteristics at 25 ppm: green, floral, woody with fruity, citrus and melon nuances
General Description
Nerolidol is a naturally occurring sesquiterpene found in the essential oils.
Flammability and Explosibility
Nonflammable
Synthesis
The natural product can be dextro- or levorotatory, whereas the synthetic product is optically inactive; the double bond at
position 6 to 7 accounts for the cis- and trans-forms.
Check Digit Verification of cas no
The CAS Registry Mumber 7212-44-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,2,1 and 2 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 7212-44:
(6*7)+(5*2)+(4*1)+(3*2)+(2*4)+(1*4)=74
74 % 10 = 4
So 7212-44-4 is a valid CAS Registry Number.
InChI:InChI=1/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/t15-/m0/s1
7212-44-4Relevant articles and documents
Stereochemical investigations on the biosynthesis of achiral (Z)-γ-bisabolene in Cryptosporangium arvum
Rinkel, Jan,Dickschat, Jeroen S.
supporting information, p. 789 - 794 (2019/04/17)
A newly identified bacterial (Z)-γ-bisabolene synthase was used for investigating the cyclisation mechanism of the sesquiterpene. Since the stereoinformation of both chiral putative intermediates, nerolidyl diphosphate (NPP) and the bisabolyl cation, is lost during formation of the achiral product, the intriguing question of their absolute configurations was addressed by incubating both enantiomers of NPP with the recombinant enzyme, which resolved in an exclusive cyclisation of (R)-NPP, while (S)-NPP that is non-natural to the (Z)-γ-bisabolene synthase was specifically converted into (E)-β-farnesene. A hypothetical enzyme mechanistic model that explains these observations is presented.
Heteropoly acid catalyzed cyclization of nerolidol and farnesol: Synthesis of α-bisabolol
De Meireles, Augusto L.P.,Costa, Maíra Dos Santos,Da Silva Rocha, Kelly A.,Gusevskaya, Elena V.
, p. 271 - 275 (2015/07/07)
Heteropoly acid H3PW12O40 is an active and environmentally friendly homogeneous catalyst for the synthesis of α-bisabolol, a high-priced and highly demanded ingredient for the fragrance, cosmetic and pharmaceutical industries, starting from more abundant biomass-based sesquiterpenic alcohols. The solvent nature remarkably affects the reaction pathways and product selectivity. In acetone solutions, α-bisabolol can be obtained in 55-60% GC yields from nerolidol and 60-70% GC yields from farnesol at complete substrate conversions, which are probably the best results ever reported for these reactions. α-Bisabolol synthesized by this method contains no farnesol, which is a potentially allergenic compound and should be avoided in the commercially used α-bisabolol. This advantage is especially important because the distillative separation of α-bisabolol and farnesol is a troublesome task. The catalyst shows high turnover numbers and operates under mild nearly ambient conditions.
Method for Converting Farnesol to Nerolidol in the Presence of Alpha-Bisabolol
-
Paragraph 0138 - 0139, (2013/11/06)
A method for converting farnesol to nerolidol in the presence of alpha-bisabolol including providing or preparing a mixture of alpha-bisabolol, farnesol, and one or more catalysts for selective isomerization of farnesol to nerolidol in the presence of alpha-bisabolol, and converting at least a portion of the farnesol to nerolidol.
