7212-44-4 Usage
Description
Nerolidol is a naturally occurring sesquiterpene alcohol with a faint, floral odor similar to rose and apple. It is found in the essential oils of neroli, ylang-ylang, and Peru balsam, and is characterized by its fresh, unusually sweet, and tenacious scent. The natural form of nerolidol can be dextroor levo-rotatory, while the synthetic version is optically inactive. The presence of a double bond at positions 6-7 results in cisand trans-forms of the compound.
Uses
Used in Flavor Industry:
Nerolidol is used as a flavor ingredient in various food products, such as baked goods, frozen dairy, nonalcoholic beverages, and soft candy, due to its pleasant and versatile aroma.
Used in Perfumery:
In the perfumery industry, nerolidol is utilized as a fragrance component, adding depth and complexity to scent compositions.
Used in Pharmaceutical Industry:
Nerolidol is used as an anti-ulcer agent, helping to alleviate the symptoms and discomfort associated with peptic ulcers.
Used in Agriculture:
As an insect antifeedant, nerolidol is employed in agricultural applications to deter pests from feeding on crops, thereby reducing crop damage and the need for chemical pesticides.
Used in Malaria Treatment:
Nerolidol has been identified as a potential and effective treatment for malaria, making it a valuable component in the development of new antimalarial drugs.
Used in Cardiac Research:
As a terpene with high potency on the contractility of cardiac muscle in guinea pig left atrium, nerolidol is used in research to better understand the mechanisms of cardiac function and to develop new treatments for heart-related conditions.
Used in Essential Oils:
Nerolidol is one of the main components in the essential oils extracted from fresh aerial parts of Thymus ciliatus (Lamiaceae), contributing to the overall aroma and potential therapeutic properties of these oils.
References
[1] George A. Burdock, Fenaroli's Handbook of Flavor Ingredients, 6th Edition, 2010
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
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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.
