| Identification | Back Directory | [Name]
Nerolidol | [CAS]
40716-66-3 | [Synonyms]
Nerolidol
trans-Form
E-Nerolidol
(E)-Nerolidol
Nerolidol (E)
Einecs 255-053-4
Trans-(E)-Nerolidol
Nerolidol trans-form
Teprenone Impurity 19
TRANS-NEROLIDOL WITH GC
trans-Nerolidal solution
Teprenone Impurity 19 (trans-Nerolidol)
(E)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol
(6E)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol
(6E)-3,7,11-Trimethyldodeca-1,6,10-trien-3-ol
(E)-3,7,11-Trimethyldodeca-1,6,10-triene-3-ol
3-Hydroxy-3,7,11-trimethyl-1,6,10-dodecatriene
1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl-, (E)-
1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl-, (6E)-
[R,Z,(-)]-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol
nerolidol,(6E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol,peruviol,trans-nerolidol
(E)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol, trans-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol
trans-Nerolidol,(E)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol, trans-3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol | [EINECS(EC#)]
255-053-4 | [Molecular Formula]
C15H26O | [MDL Number]
MFCD00008911 | [MOL File]
40716-66-3.mol | [Molecular Weight]
222.37 |
| Chemical Properties | Back Directory | [Boiling point ]
145-146 °C12 mm Hg(lit.)
| [density ]
0.876 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.479(lit.)
| [Fp ]
230 °F
| [storage temp. ]
-20°C | [solubility ]
DMF: miscible,DMSO: miscible,Ethanol: miscible,Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml | [form ]
neat | [pka]
14.40±0.29(Predicted) | [color ]
Colorless to light yellow | [Odor]
at 100.00 %. floral green citrus woody waxy | [Odor Type]
floral | [JECFA Number]
1646 | [Merck ]
13,6501 | [BRN ]
5731231 | [Stability:]
Light Sensitive | [Major Application]
food and beverages | [Cosmetics Ingredients Functions]
PERFUMING | [InChI]
1S/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/b14-11+ | [InChIKey]
FQTLCLSUCSAZDY-SDNWHVSQSA-N | [SMILES]
C\C(C)=C/CC\C(C)=C\CCC(C)(O)C=C | [LogP]
5.316 (est) | [NIST Chemistry Reference]
1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl-, (e)-(40716-66-3) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26-36 | [RIDADR ]
UN1230 - class 3 - PG 2 - Methanol, solution | [WGK Germany ]
1
| [F ]
10-23 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Aquatic Acute 1
Aquatic Chronic 1
Eye Irrit. 2
Skin Sens. 1B | [Toxicity]
Both the acute oral LD50 in rats and the acute dermal LD50 in rabbits exceeded 5 g/kg (Russell. 1973). |
| Hazard Information | Back Directory | [Description]
trans-Nerolidol is a sesquiterpene that has been found in various plants, including C. sativa, and has diverse biological activities, including antimicrobial, antioxidant, anticancer, and insecticidal properties.1,2,3,4 In a disc assay, trans-nerolidol inhibits the growth of S. aureus, B. subtilis, E. coli, and S. cerevisiae with zones of inhibition measuring 10, 9, 10, and 4 mm, respectively.2 It reduces viability of CaCo-2 adenocarcinoma cells with an IC50 value of 28.7 mg/L and reduces production of reactive oxygen species (ROS).3 trans-Nerolidol is insecticidal against A. aegypti larvae with a 24-hour LC50 value of 9 mg/L.4 | [Occurrence]
Reported to be found in cabreuva oil, oil of neroli, balsam Peru, ylang ylang and many others (Gildemeister & Hoffman, 1959). | [Uses]
Nerolidol (cas# 40716-66-3) is a terpene standard found in cannabis. | [Definition]
ChEBI: 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. | [Preparation]
By isolation from a suitable essential oil or by chemical synthesis. | [References]
[1] LORENZO NISSEN . Characterization and antimicrobial activity of essential oils of industrial hemp varieties (Cannabis sativa L.)[J]. Fitoterapia, 2010, 81 5: Pages 413-419. DOI: 10.1016/j.fitote.2009.11.010
[2] H D SKALTSA. Composition and antimicrobial activity of the essential oil of Scutellaria albida ssp. albida from Greece.[J]. Planta medica, 2000, 66 7: 672-674. DOI: 10.1055/s-2000-8650
[3] MARTIN AMBRO?. The Influence of Sesquiterpenes from Myrica rubra on the Antiproliferative and Pro-Oxidative Effects of Doxorubicin and Its Accumulation in Cancer Cells.[J]. Molecules, 2015, 20 8: 15343-15358. DOI: 10.3390/molecules200815343
[4] J. CHANTRAINE. Insecticidal activity of essential oils on Aedes aegypti larvae[J]. Phytotherapy Research, 1998, 64 3. DOI: 10.1002/(sici)1099-1573(199808)12:5<350::aid-ptr311>3.0.co;2-7 |
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