Nerolidol

Nerolidol Basic information
Description References
Product Name:Nerolidol
Synonyms:TRANS-3,7,11-TRIMETHYL-1,6,10-DODECATRIEN-3-OL;(CIS AND TRANS)-NEROLIDOL;FEMA 2772;3-HYDROXY-3,7,11-TRIMETHYL-1,6,10-DODECATRIENE,3,7,11-TRIMETHYL-1,6,10-DODECATRIEN-3-OL;10-dodecatrien-3-ol,3,7,11-trimethyl-6;3,7,11-trimethyl-1,6,10-dodecatrien-3-ol (nerolidol);3,7,11-Trimethyl-1,6,10-dodecatriene-3-ol;3,7,11-trimethyl-dodeca-1,6,10-trien-3-ol
CAS:7212-44-4
MF:C15H26O
MW:222.37
EINECS:230-597-5
Product Categories:Biochemistry;Terpenes;Terpenes (Others);Chamaemelum nobile (Chamomile tea);Panax ginseng;Acyclic;Alkenes;Building Blocks;Chemical Synthesis;Citrus aurantium (Seville orange);Elettaria Cardamomum (Cardamom);Humulus lupulus (Hops);Nutrition Research;Ocimum basilicum (Basil);Organic Building Blocks;Phytochemicals by Plant (Food/Spice/Herb);bc0001
Mol File:7212-44-4.mol
Nerolidol Structure
Nerolidol Chemical Properties
Melting point -75 °C
Boiling point 114 °C/1 mmHg (lit.)
density 0.875 g/mL at 25 °C (lit.)
vapor pressure <1 hPa (20 °C)
refractive index n20/D 1.479(lit.)
FEMA 2772 | NEROLIDOL (ISOMER UNSPECIFIED)
Fp 230 °F
storage temp. Store below +30°C.
solubility 0.014g/l
form Liquid
pka14.44±0.29(Predicted)
color Clear slightly yellow
Odorat 100.00 %. floral green waxy citrus woody
Odor Typefloral
explosive limit0.7-4.5%(V)
Water Solubility immiscible
Merck 14,6476
JECFA Number1646
BRN 1724135
LogP4.5 at 24℃
CAS DataBase Reference7212-44-4(CAS DataBase Reference)
NIST Chemistry Reference1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl-(7212-44-4)
EPA Substance Registry SystemNerolidol (7212-44-4)
Safety Information
Hazard Codes Xi,N
Risk Statements 36/37/38-50/53
Safety Statements 26-36-61-60
RIDADR UN 3082 9 / PGIII
WGK Germany 2
RTECS JR4977000
10-23
Autoignition Temperature230 °C
TSCA Yes
HS Code 29052290
ToxicityLD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 5000 mg/kg
MSDS Information
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Nerolidol English
SigmaAldrich English
ACROS English
ALFA English
Nerolidol Usage And Synthesis
DescriptionNerolidol 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.
References[1] George A. Burdock, Fenaroli's Handbook of Flavor Ingredients, 6th Edition, 2010
DescriptionNerolidol 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.
Chemical PropertiesNerolidol 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.
Chemical PropertiesClear slightly yellow liquid
Chemical PropertiesNerolidol has a faint, fresh, unusually sweet, tenacious, floral odor similar to rose and appe
OccurrenceReported 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.
Usesanti-ulcer, insect antifeedant
UsesNerolidol 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.
DefinitionChEBI: Nerolidol is a farnesane sesquiterpenoid that is dodeca-1,6,10-triene which carries methyl groups at positions 3, 7 and 11 and a hydroxy group at position 3. It is a natural product that is present in various flowers and plants with a floral odor. Chemically, it exists in two geometric isomers, trans and cis forms. It is widely used in cosmetics (e.g. shampoos and perfumes), in non-cosmetic products (e.g. detergents and cleansers) and also as a food flavoring agent. It has a role as a flavouring agent, a cosmetic, a pheromone, a neuroprotective agent, an antifungal agent, an anti-inflammatory agent, an antihypertensive agent, an antioxidant, a volatile oil component, an insect attractant and a herbicide. It is a farnesane sesquiterpenoid, a tertiary allylic alcohol and a volatile organic compound.
Aroma threshold valuesDetection: 10 ppb to 10 ppm
Taste threshold valuesTaste characteristics at 25 ppm: green, floral, woody with fruity, citrus and melon nuances
General DescriptionNerolidol is a naturally occurring sesquiterpene found in the essential oils.
Flammability and ExplosibilityNonflammable
SynthesisThe 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.
Nerolidol Preparation Products And Raw materials
Raw materialsNeroli oil-->Peru balsam-->Orange sweet oil
Preparation ProductsFARNESOL-->Cyclohexene, 1-methyl-4-(5-methyl-1-methylene-4-hexen-1-yl)--->2Z,6Z-Farnesol
Ethanol Diniconazole 1-Dodecanol Geranyl linalool CYCLODODECENE CIS-NEROLIDOL,NEROLIDOL, CIS-,(Z)-Nerolidol,(S)-cis-nerolido Nerolidol NEROLIDYL PROPIONATE NEROLIDOL, CIS-,(Z)-nerolidol,(6Z)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol,cis-nerolidol,NEROLIDOL, cis-(SG),CIS-NEROLIDOL WITH GC,CIS-NEROLIDOL Norandrostenedione Nerolidol, acetate 4-(4,8-DIMETHYL-3,7-NONADIENYL)-5-METHYLENE-4-METHYL-1,3-DIOXOLANE-2-ONE NEROLIDOL NATURAL Allyl methacrylate NEROLIDYL ISOBUTYRATE Trans-(E)-Nerolidol,Nerolidol,nerolidol,(6E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol,peruviol,trans-nerolidol,TRANS-NEROLIDOL WITH GC,(E)-Nerolidol,E-Nerolidol Cyclododeca-1,5,9-triene METHYLCYCLOPENTADIENE DIMER

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