Nerolidol
Synonym(s):3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol;3-Hydroxy-3,7,11-trimethyl-1,6,10-dodecatriene;Nerolidol
- CAS NO.:40716-66-3
- Empirical Formula: C15H26O
- Molecular Weight: 222.37
- MDL number: MFCD00008911
- EINECS: 255-053-4
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-19 23:02:33
What is Nerolidol?
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. 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. 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). trans-Nerolidol is insecticidal against A. aegypti larvae with a 24-hour LC50 value of 9 mg/L.
Occurrence
Reported to be found in cabreuva oil, oil of neroli, balsam Peru, ylang ylang and many others (Gildemeister & Hoffman, 1959).
The Uses of Nerolidol
Nerolidol (cas# 40716-66-3) is a terpene standard found in cannabis.
Preparation
By isolation from a suitable essential oil or by chemical synthesis.
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.
Properties of Nerolidol
Boiling point: | 145-146 °C12 mm Hg(lit.) |
Density | 0.876 g/mL at 25 °C(lit.) |
refractive index | n |
Flash point: | 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) |
form | Liquid |
color | Colorless to light yellow |
Odor | at 100.00 %. floral green citrus woody waxy |
JECFA Number | 1646 |
Merck | 13,6501 |
BRN | 5731231 |
Stability: | Light Sensitive |
NIST Chemistry Reference | 1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl-, (e)-(40716-66-3) |
Safety information for Nerolidol
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 Environment GHS09 |
GHS Hazard Statements |
H317:Sensitisation, Skin H319:Serious eye damage/eye irritation H410:Hazardous to the aquatic environment, long-term hazard |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Nerolidol
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