Synonym name: 3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol; Peruviol; Melaleucol; Humbertiol
Catalogue No.: BP0996
Cas No.: 7212-44-4
Formula: C15H26O
Mol Weight: 222.372
Botanical Source: A component of many essential oils
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
Nerolidol (CAS number: 7212-44-4) is a naturally occurring sesquiterpene compound widely distributed in essential oils of various aromatic plants, such as orange blossom, lemongrass, turmeric, and certain pine plants. As a membrane active sesquiterpene, nerolidol has attracted much attention due to its diverse biological activities, especially in the fields of anti-cancer, anti-inflammatory, antibacterial, and antiparasitic effects, showing significant pharmacological potential. In recent years, with the deepening development of natural product pharmacology, the biological functions and mechanisms of action of nerolidol have gradually been elucidated, especially in the research of neuroprotection and anti anxiety, breakthrough progress has been made. The purpose of this article is to systematically review the chemical structure, sources, pharmacological activity, target of action, and pharmacological characteristics of nerolidol, explore its clinical application prospects, and provide theoretical basis for subsequent research and new drug development.
Orange blossom tertiary alcohol is a sesquiterpene alcohol containing 15 carbon atoms, with a molecular formula of C15H26O and a molecular weight of 222.3720. Its structural feature is a linear allyl skeleton containing two unsaturated double bonds and a tertiary alcohol functional group. Orange blossom tertiary alcohol exists in two geometric isomers, namely cis and trans isomers, which have slight differences in natural sources and biological activity.
In terms of physical and chemical properties, the LogP value of orange blossom tertiary alcohol is 4.9085, indicating its strong lipid solubility, which helps it penetrate biological membranes and the blood-brain barrier (BBB), thereby exerting its effects in the central nervous system. Its polar surface area (TPSA) is only 20.23 Å ², further supporting its excellent membrane permeability. Low water solubility (0.0072 mg/mL) suggests that its distribution in vivo mainly depends on lipid mediators. It is worth noting that nerolidol did not exhibit hERG channel inhibitory activity, and the Ames mutagenicity test was negative, indicating its high safety and good potential for drug development.
Orange blossom tertiary alcohol is widely present in the essential oils of various aromatic plants, especially in Citrus aurantium, Cymbopogon citratus, Curcuma longa, and certain pine plants such as the genus Pinus. Its content is greatly influenced by plant species, growth environment, harvesting period, and extraction process.
The traditional extraction methods mainly include distillation and solvent extraction. Steam distillation is the most commonly used industrial extraction technique, which can effectively separate volatile components and obtain high-purity orange blossom tertiary alcohol. In recent years, supercritical CO2 extraction technology has gradually become a new trend in the extraction of orange blossom tertiary alcohols due to its advantages of environmental friendliness, strong selectivity, and mild operation. In addition, molecular distillation and high-performance liquid chromatography (HPLC) techniques have also been used for the purification and quantitative analysis of nerolidol.
Orange blossom tertiary alcohol exhibits significant anti-tumor activity in various cancer models. In vitro studies have shown that nerolidol can induce apoptosis of tumor cells, inhibit cell proliferation and migration, involving mechanisms such as cell cycle arrest, loss of mitochondrial membrane potential, and increased generation of reactive oxygen species (ROS). It has inhibitory effect on breast cancer, liver cancer and colorectal cancer cell lines. In vivo experiments, nerolidol significantly delayed tumor growth by regulating the tumor microenvironment and immune response.
Orange blossom tertiary alcohol can effectively inhibit the release of various inflammatory mediators, such as tumor necrosis factor - α (TNF - α), interleukin-6 (IL-6), and nitric oxide (NO). Its anti-inflammatory mechanism mainly involves inhibiting the nuclear factor kappa B (NF - κ B) signaling pathway and reducing the expression of pro-inflammatory enzymes (COX-2, iNOS), reducing inflammatory cell infiltration, and alleviating tissue damage. Animal models have shown that nerolidol can play a protective role in arthritis, enteritis, and skin inflammation.
Orange blossom tertiary alcohol exhibits inhibitory effects on various bacteria and fungi, especially sensitive to Gram positive bacteria such as Staphylococcus aureus and Streptococcus. Its antibacterial mechanism involves cell membrane disruption and metabolic disorders. In addition, orange blossom tertiary alcohol has a significant inhibitory effect on parasites such as blood sucking worms, nematodes, and malaria parasites, which can interfere with the life activities and reproduction of parasites, demonstrating potential value for the development of antiparasitic drugs.
Orange blossom tertiary alcohol can protect cells from lipid peroxidation, protein oxidation, and DNA damage, especially showing significant protective effects on mouse hippocampal neurons. Its antioxidant capacity helps alleviate the pathological process of neurodegenerative diseases. More importantly, nerolidol has shown positive effects in anti anxiety, and animal behavioral experiments have shown that it can improve anxiety like behavior, suggesting its potential to regulate central nervous system function.
The multi-target mechanism of action of orange blossom tertiary alcohol is the basis for its broad pharmacological activity. Regarding the anti anxiety effect, research has revealed that its main targets include:
In addition, orange blossom tertiary alcohol reduces neuronal damage and enhances neuroprotective effects by regulating oxidative stress-related signaling pathways. In the process of anti-cancer and anti-inflammatory, its mechanism of action involves regulating apoptosis related proteins (such as Bcl-2 family), inhibiting NF - κ B and MAPK signaling pathways, and reducing the expression of pro-inflammatory factors.
Orange blossom tertiary alcohol has good medicinal properties. Its molecular weight is 222.37, which conforms to the ideal range of Lipinski rule. High lipid solubility (LogP about 4.9) is beneficial for oral absorption and cell membrane penetration, and the low polarity surface area (TPSA 20.23) supports its excellent biofilm permeability. Low water solubility suggests the need for appropriate formulation techniques to improve its bioavailability.
Pharmacokinetic studies have shown that nerolidol can effectively penetrate the blood-brain barrier and reach the central nervous system, making it suitable for the treatment of neurological related diseases. Metabolism in the body is mainly carried out through the liver enzyme system, and the safety of metabolites is good. The hERG channel inhibition test was negative, indicating a low risk of cardiac toxicity. The Ames test results showed no mutagenicity and high safety.
However, the low water solubility and potential metabolic instability of orange blossom tertiary alcohol are the main challenges in its clinical development, which need to be addressed through modern drug delivery systems such as nanocarriers, liposomes, or solid dispersions.
Orange blossom tertiary alcohol, as a multifunctional natural product, has broad clinical application potential. Its anti-cancer, anti-inflammatory, and antiparasitic activities provide new drug candidate molecules for tumor treatment, chronic inflammatory diseases, and parasitic infections. Especially in the fields of neuroprotection and anti anxiety, the high blood-brain barrier penetration ability and multi-target regulatory mechanism of nerolidol make it a strong competitor in the development of drugs for the treatment of central nervous system diseases.
Future research should focus on pharmacokinetic optimization, dosage form innovation, and clinical safety evaluation of nerolidol. At the same time, by combining modern molecular biology and computational pharmacology techniques, we can deeply analyze its mechanism of action and target network, providing theoretical support for precision drug design. In addition, the synergistic effect of orange blossom tertiary alcohol with other drugs and its application in compound preparations also deserve further exploration.
Orange blossom tertiary alcohol, as a natural sesquiterpene alcohol, has shown broad pharmacological research and clinical application prospects due to its unique chemical structure and rich biological activity. Its functions in anti-cancer, anti-inflammatory, antibacterial, antiparasitic, and neuroprotective aspects provide valuable resources for the development of natural product drugs. In the future, through systematic pharmacological mechanism research and drug optimization, nerolidol is expected to become an important representative of the new generation of multifunctional natural medicines, promoting the integrated development of natural product pharmacology and modern drug research and development.
