Nerol

154.25

154.25

1722455

203-378-7

38G5P53250

DTXSID3026728

Colorless oily liquid|Liquid

29052210

20.2

2.9

Clear colorless to almost colorless Liquid

0.8756 g/cm³ @ Temp: 20 °C

<-15 °C

225 °C

226 °F

n 20/D 1.474(lit.)

absolute ethanol: soluble(lit.)

2-8°C

3.0X01-2 mm Hg at 25 deg C (extrapolated)

The acute oral LD 50 value in rats was reported as 4.5 g/kg (3.4-5.6 g/kg) (Moreno, 1972). The acute dermal LD 50 value in rabbits exceeded 5 g/kg (Moreno, 1972).

Sweet rose

Bitter flavor

Henry's Law constant = 1.15X10-5 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 1.80X10-10 cu cm/molec-sec at 25 °C (est)|Atmospheric ozone reaction rate constant = 8.6X10-16 cu cm/molec-sec at 25 °C (est)

UN1230 - class 3 - PG 2 - Methanol, solution

2

36/37/38

26-36

RG5840000

Xi

Chemical stability: Stable under recommended storage conditions.

P261-P305 + P351 + P338

H315-H319-H335

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.

Strong oxidizing agents

Nerol is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and b) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Lapczynski A et al; Fragrance material review on nerol. Food Chem Toxicol 46(Suppl 11): S241-4 (2008). Fragrance material review on nerol.[Lapczynski A et al; Fragrance material review on nerol. Food Chem Toxicol 46(Suppl 11): S241-4 (2008).]

|Danger|H315 (97.23%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P280, P302+P352, P305+P351+P338, P310, P321, P332+P313, P333+P313, P337+P313, P362, P363, and P501|Aggregated GHS information provided by 2098 companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P280, P302+P352, P305+P351+P338, P310, P321, P332+P313, P333+P313, P362, P363, and P501|Warning|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501

Eye/face protection: Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.|Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Absorb on sand or vermiculite and place in closed containers for disposal. Ventilate area and wash spill site after material pickup is complete.|ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Do not let product enter drains.|Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

Avoid contact with skin and eyes. Avoid inhalation of vapor or mist.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

Nerol resulted in moderate skin irritation.|Skin irritation: Nerol applied full strength to intact or abraded rabbit skin for 24 hours produced moderate irritation.|A skin irritant.

Nerol has been identified as a component of tobacco smoke(1).

IDENTIFICATION AND USE: Nerol is a colorless oily fluid. Nerol is reported to be found in neroli oil (with geraniol) and in many essential oils. It used as a base for the manufacture of perfumes and in fragrances. HUMAN EXPOSURE AND TOXICITY: A single sensitization test was carried out on 25 volunteers. The material was tested at a concentration of 4% in petrolatum and produced no sensitization reactions. In other study, nerol was utilized in a closed patch test on the back or forearm of 314 subjects for 24-48 hr. Slight erythema was demonstrated in 10 (3.19%) subjects. In an in vitro chromosome aberration test in cultured human lymphocytes nerol was not clastogenic with and without metabolic activation. ANIMAL STUDIES: Eye irritant effects were observed in rabbits. Slight skin irritation was observed in guinea pigs and rabbits. Respiratory irritation was assessed in mice by recording their respiratory rate when exposed to nerol. Mice were exposed to the test material for 1 min using a nebulizer for aerosolization in a 2600 mL chamber. Mild to moderate decrease in the respiratory rate was observed, and the ED25 (dose at which there is a 25% reduction in the respiratory rate) was calculated to be 591 ug /L. Rats (10 males/dose) were administered the test substance at 2560 - 9800 mg/kg and observed for 14 days. The numbers of deaths per dose were 1, 4, 7 and 10 at 2560, 4000, 6250 and 9800 mg/kg-bw, respectively. All deaths occurred within two days of dose administration. Clinical signs in rats included exophthalmia, hyperflexiveness, restlessness, lethargy and loss of righting reflex. Nerol was not mutagenic in Salmonella typhimurium (TA 1535, TA 1537, TA 98, TA 100 and TA 102) with or without activation. In an in vitro mammalian cell gene mutation test with mouse lymphoma cells nerol was not mutagenic at the hprt locus of L5178Y mouse lymphoma cells, in the presence and absence of metabolic activation.

Oral carcinogenesis, a multistep process with multifaceted etiology, arises due to accumulation of heterogeneous genetic changes in the genes involved in the basic cellular functions including cell division, differentiation, and cell death. These genetic changes in the affected cell progressively increase the cell proliferation, angiogenesis, and inhibition of apoptosis. The present study investigated the modulating effect of geraniol on the expression pattern of cell proliferative (PCNA, cyclin D1, c-fos), inflammatory (NF-kappaB, COX-2), apoptotic (p53, Bax, Bcl-2, caspase-3 and -9), and angiogenic (VEGF) markers in 7,12-dimethylbenz[a]anthracene (DMBA)-induced hamster buccal pouch carcinogenesis. Topical application of 0.5 % DMBA in liquid paraffin, three times a week, for 14 weeks, developed well-differentiated squamous cell carcinoma (SCC) in the buccal pouch of golden Syrian hamsters. All the hamsters treated with DMBA alone (100 %) developed oral tumors in the buccal pouch after 14 weeks. Over-expression of mutant p53, PCNA, Bcl-2, and VEGF accompanied by decreased expression of Bax were noticed in hamsters treated with DMBA alone. Increased expression of c-fos, COX-2, NF-kappaB, and cyclin D1 and decreased activities of caspase-3 and -9 were also noticed in hamsters treated with DMBA alone. Oral administration of geraniol at a dose of 250 mg/kg bw (body weight) not only completely prevented the formation of oral tumors but also prevented the deregulation in the expression of above mentioned molecular markers in hamsters treated with DMBA. The present results thus suggest that geraniol has potent anti-inflammatory, anti-angiogenic, anti-cell proliferative, and apoptosis-inducing properties in DMBA-induced hamster buccal pouch carcinogenesis. /Geraniol/|Geraniol (GO) potent antitumor and chemopreventive effects are attributed to its antioxidant and anti-inflammatory properties. In the current study, the potential efficacy of GO (250 mg/kg) in ameliorating metabolic syndrome (MetS) induced by fructose in drinking water was elucidated. Moreover, the effect of pioglitazone (5 and 10 mg/kg; PIO) and the possible interaction of the co-treatment of GO with PIO5 were studied in the MetS model. After 4 weeks of treatment, GO and/or PIO reduced the fasting blood glucose and the glycemic excursion in the intraperitoneal glucose tolerance test. GO and PIO5/10 restrained visceral adiposity and partly the body weight gain. The decreased level of peroxisome proliferator activated receptor (PPAR)-gamma transcriptional activity in the visceral adipose tissue of MetS rats was increased by single treatment regimens. Though GO did not affect MetS-induced hyperinsulinemia, PIO5/10 lowered it. Additionally, GO and PIO5/10 suppressed glycated hemoglobin and the receptor for advanced glycated end products (RAGE). These single regimens also ameliorated hyperuricemia, the disrupted lipid profile, and the elevated systolic blood pressure evoked by MetS. The rise in serum transaminases, interleukin-1beta, and tumor necrosis factor-a, as well as hepatic lipid peroxides and nitric oxide (NO) was lowered by the single treatments to different extents. Moreover, hepatic non-protein thiols, as well as serum NO and adiponectin were enhanced by single regimens. Similar effects were reached by the combination of GO with PIO5; however, a potentiative interaction was noted on fasting serum insulin level, while synergistic effects were reflected as improved insulin sensitivity, as well as reduced RAGE and triglycerides. Therefore, GO via the transcriptional activation of PPAR-gamma reduces inflammation and free radical injury produced by MetS. Thereby, these effects provide novel mechanistic insights on GO management of MetS associated critical risk factors. Moreover, the co-administration of GO to PIO5 exalted the antidiabetic drug anti-MetS efficacy. /Geraniol/|In the recent past, several phytoconstituents are being explored for their potential neuromodulatory effects in neurological diseases. Repeated exposure of acrylamide (ACR) leads to varying degree of neuronal damage in experimental animals and humans. In view of this, the present study investigated the efficacy of geraniol (GE, a natural monoterpene) to mitigate acrylamide (ACR)-induced oxidative stress, mitochondrial dysfunction and neurotoxicity in a rat model and compared its efficacy to that of curcumin (CU, a spice active principle with multiple biological activities). ACR administration (50mg/kg bw, i.p. 3times/week) for 4weeks to growing rats caused typical symptoms of neuropathy. ACR rats provided with daily oral supplements of phytoconstituents (GE: 100mg/kg bw/d; CU: 50mg/kg bw/d, 4weeks) exhibited marked improvement in behavioral tests. Both phytoconstituents markedly attenuated ACR-induced oxidative stress as evidenced by the diminished levels of reactive oxygen species, malondialdehyde and nitric oxide and restored the reduced glutathione levels in sciatic nerve (SN) and brain regions (cortex - Ct, cerebellum - Cb). Further, both phytoconstituents effectively diminished ACR-induced elevation in cytosolic calcium levels in SN and Cb. Furthermore, diminution in the levels of oxidative markers in the mitochondria was associated with elevation in the activities of antioxidant enzymes. While ACR mediated elevation in the acetylcholinesterase activity was reduced by both actives, the depletion in dopamine levels was restored only by CU in brain regions. Taken together our findings for the first time demonstrate that the neuromodulatory propensity of GE is indeed comparable to that of CU and may be exploited as a therapeutic adjuvant in the management of varied human neuropathy conditions. /Geraniol/|The present studies were performed to compare the differences between sensitization potency of fragrance mix and its ingredients (oak moss absolute, isoeugenol, eugenol, cinnamal, hydroxycitronellal, geraniol, cinnamic alcohol, alpha amyl cinnamal), by using ex vivo LLNA-BrdU ELISA. The SI and EC3 values were calculated and potency classification was found for the mixture and for each ingredients. TH1 cytokines (IL-2, IFN-?) and TH2 cytokines (IL-4, IL-5) releases from lymph node cell culture were also investigated as contact sensitization endpoints. The EC3 values were calculated and the potency of contact sensitization were classified for fragrance mix, oak moss absolute, isoeugenol, eugenol, cinnamal, hydroxycitronellal, geraniol, cinnamic alcohol, alpha amyl cinnamal respectively: 4.4% (moderate), 3.4% (moderate), 0.88% (strong), 16.6% (weak), 1.91% (moderate), 9.77% (moderate), 13.1% (weak), 17.93% (weak), 7.74% (moderate). According to our results it should be concluded that exposure to fragrance mix does not constitute an evidently increased hazard compared to exposure to each of the eight fragrance ingredients separately. Cytokine analyses results indicate that both TH1 and TH2 cytokines are involved in the regulation of murine contact allergy and can be considered as useful endpoints. /Geraniol/|For more Interactions (Complete) data for Nerol (6 total), please visit the HSDB record page.

LD50 Rat Oral 4.5 g/kg|LD50 Rabbit dermal > 5000 mg/kg|LD50 Mouse intramuscular 3000 mg/kg

Nerol occurs in many essential oils in small quantities where it is always accompanied by geraniol(1). Nerol has been detected in a wide variety of plants and species(2).

Nerol's production and use as a fragrance ingredient, as an intermediate in the synthesis of other fragrance chemicals(1) and as a flavoring compound in foods(2) may result in its release to the environment through various waste streams(SRC). Its use as a fragrance ingredient in perfumes and household products(1) will result in its direct release to the environment(SRC). Nerol has been identified as a component of tobacco smoke(3).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 94(SRC), determined from a structure estimation method(2), indicates that nerol is expected to have high mobility in soil(SRC). Volatilization of nerol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-5 atm-cu m/mole(SRC), derived from its extrapolated vapor pressure, 0.03 mm Hg(2), and water solubility, 531 mg/L(3). Even though the vapor pressure is low environmentally at standard temperature and pressure, there is a detectable odor; therefore, nerol may volatilize from dry soil(SRC). Utilizing the OECD 301D test (closed bottle), 80% of the Theoretical BOD was reached in 4 weeks(5) indicating that biodegradation is an important environmental fate process. Two screening tests found mixtures of nerol and geraniol to be readily biodegradable based on 100% degradation after 28 and 15 days(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 94(SRC), determined from a structure estimation method(2), indicates that nerol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.2X10-5 atm-cu m/mole(SRC), derived from its extrapolated vapor pressure, 0.03 mm Hg(2), and water solubility, 531 mg/L(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4.1 and 34 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 90(SRC), from its log Kow of 3.47(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Utilizing the OECD 301D test (closed bottle) and a river water inoculum, 80% of the Theoretical BOD was reached in 4 weeks(7) indicating that biodegradation is an important environmental fate process. Two screening tests found mixtures of nerol and geraniol to be readily biodegradable based on 100% degradation after 28 and 15 days(8). Nerol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Nerol is an olefin and olefins in surface waters exposed to sunlight react with photo-oxidants (such as hydroxyl radicals, peroxy radicals and singlet oxygen) with a half-life on the order of 25 days(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), nerol, which has an extrapolated vapor pressure of 0.03 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase nerol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.1 hours(SRC), calculated from its rate constant of 1.8X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Vapor-phase nerol is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 19 minutes(SRC), calculated from its rate constant of 8.6X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Vapor-phase nerol is degraded in the atmosphere by reaction with nitrate radicals(SRC); the half-life for this reaction in air is estimated to be 4 minutes(SRC), calculated from a rate constant of 1.66X10-11 cu cm/molecule-sec at 24 °C for the analogous compound geraniol(3). The nitrate radical (NO3) is the dominant atmospheric oxidant during the night-time in most atmospheric environments(4), therefore, night-time degradation appears to be a major fate process for nerol(SRC).

The rate constant for the vapor-phase reaction of nerol with photochemically-produced hydroxyl radicals has been estimated as 1.8X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.1 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of nerol with atmospheric ozone has been estimated as 8.6X10-16 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1); this corresponds to an atmospheric half-life of about 19 minutes at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(1). By analogy to a measured rate constant geraniol(2), the rate constant for the vapor-phase reaction of nerol with atmospheric nitrate radicals is estimated as 1.66X10-11 cu cm/molecule-sec at 24 °C(SRC); this corresponds to an atmospheric half-life of about 4 minutes(SRC) at an atmospheric concentration of 2.5X10+8 nitrate radicals per cu cm(3). The nitrate radical (NO3) is the dominant atmospheric oxidant during the night-time in most atmospheric environments(4), therefore, night-time degradation appears to be a major fate process for nerol(SRC). Nerol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(5). Nerol is an olefin and olefins in surface waters exposed to sunlight react with photo-oxidants (such as hydroxyl radicals, peroxy radicals and singlet oxygen) with a half-life on the order of 25 days(6).

An estimated BCF of 90 was calculated in fish for nerol(SRC), using a log Kow of 3.47(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of nerol can be estimated to be 94(SRC). According to a classification scheme(2), this estimated Koc value suggests that nerol is expected to have high mobility in soil.

The Henry's Law constant for nerol is estimated as 1.2X10-5 atm-cu m/mole(SRC) derived from its extrapolated vapor pressure, 0.03 mm Hg(1), and water solubility, 531 mg/L(2). This Henry's Law constant indicates that nerol is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 4.1 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 34 days(SRC). Nerol's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Even though the vapor pressure is low environmentally at standard temperature and pressure, there is a detectable odor; therefore, nerol may volatilize from dry soil(SRC). Patch testing to determine the evaporation rate of fragrance chemicals from skin found that evaporation of geraniol (a terpenoid very similar to nerol) was not sensitive to pH changes from 4.0 to 7.0 and that 8.9-39% of applied geraniol was lost within 40 minutes to 24 hours(5).

Nerol was identified in Sicilian Muscat wines(1). Nerol was detected in the volatile components of pineapple guava(2). Nerol was detected in the volatile compounds from edible Korean Chamchwi (Aster scaber Thunb)(3).

According to the 2012 TSCA Inventory Update Reporting data, 2 reporting facilities estimate the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of nerol may be as low as 25-49 workers up to the range of 50-99 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 13,881 workers (7,957 of these were female) were potentially exposed to nerol in the US(1). Occupational exposure to nerol may occur through inhalation and dermal contact with this compound at workplaces where nerol is produced or used. Monitoring and use data indicate that the general population may be exposed to nerol via inhalation of ambient air, ingestion of food, and dermal contact with consumer products containing nerol(SRC).

Vet: Antineoplastic and antiviral properties detected against chick lymphoma and avian leukosis in chicks.|Found to be useful as a sedative and spasmolytic agent in doses of 0.01- 1 g.|Vet: Vasodilator action in dogs, rabbits, and mice.|Pharmacology of Nerol: The search for therapeutic agents that will provide the ground for man and an improvement in their quality of life is ceaseless. The nerol (cis-2,6-dimethyl- 2,6-octadien-8-ol) is a monoterpene which can be found in various medicinal plants as Lippia spp and Melissa officinalis L. The objective of this study was to analyze the acute effect of nerol in the central nervous system (CNS) by performing behavioral tests in mice (open field, elevated plus-maze, light/dark and rota rod tests). We used male albino mice (Mus musculus), Swiss variety, adult with 2 month-old. The animals were divided into five groups (n = 8) for each experimental protocol, and they were administered intraperitoneally (i.p.), respectively, Tween 80 0.05% dissolved in saline solution 0.9%, nerol (30, 60 or 90 mg/kg) or diazepam (2 mg/kg). In the open field test, all groups treated with nerol showed a significant decrease in motor activity (number of crossings, rearings and groomings) when compared with vehicle group. In the elevated plus-maze test, nerol groups significantly increased the number of entries and time of permanence in the open arms when compared with vehicle group. In the light-dark test, nerol groups showed a significant increase the time of permanence in the room clear when compared with vehicle group. In the rota rod test, the groups treated with nerol didn't show modification in time spent and number of falls in the revolving bar when compared with vehicle group. These results indicate a possible anxiolytic effect of nerol in mice.|For more Therapeutic Uses (Complete) data for Nerol (8 total), please visit the HSDB record page.

As a part of corresponding study on the effects of test material on the motility of mice (groups of four 4- to 6-week old and 6-month-old female outbred Swiss mice), concentrations of test material in blood samples were determined after inhalation exposure. Air was passed into the cage through a glass tube containing 1.5 mL of test material for a total test material volume of 20-50 mg. Blood samples were taken from the animals after 0, 30, 60 and 90 minutes of inhalation exposure. The concentration of nerol in blood sample 1 hr following inhalation was 5.7 ng/mL.

Biotransformation of nerol by larvae of the common cutworm (Spodoptera litura) was investigated. The resulting major metabolites were (2Z,6E)-1-hydroxy-3,7-dimethyl-2,6-octadien-8-oic acid and 8-hydroxynerol, and the minor metabolites were 9-hydroxynerol and (2Z,6E)-1-hydroxy-3,7-dimethyl-2,6-octadien-8-al. (2Z,6E)-1-Hydroxy-3,7-dimethyl-2,6-octadien-8-oic acid is a novel compound. The results indicate that biotransformation of nerol by S. litura larvae involved 2 pathways; the main pathway involved oxidation at the methyl group of the geminal dimethyl at C-8 position followed by carboxylation, and the minor pathway involved oxidation at the methyl group of the geminal dimethyl at C-9 position.|The biotransformation of geraniol, nerol and citral by Aspergillus niger was studied. A comparison was made between submerged liquid, sporulated surface cultures and spore suspensions. This bioconversion was also carried out with surface cultures of Penicillium sp. The main bioconversion products obtained from geraniol and nerol by liquid cultures of A. niger were linalool and alpha-terpineol. Linalool, alpha-terpineol and limonene were the main products obtained from nerol and citral by sporulated surface cultures, whereas geraniol was converted predominantly to linalool, also resulting in higher yields. Bioconversion of nerol with Penicillium chrysogenum yielded mainly alpha-terpineol and some unidentified compounds. With P. rugulosum the major bioconversion product from nerol and citral was linalool. The bioconversion of nerol to alpha-terpineol and linalool by spore suspensions of A. niger was also investigated. Finally the biotransformation with sporulated surface cultures was also monitored by solid phase microextraction (SPME). It was found that SPME is a very fast and efficient screening technique for biotransformation experiments.|Allylic alcohols, such as geraniol 1, are easily oxidized by varying mechanisms, including the formation of both 2,3-epoxides and/or aldehydes. These epoxides, aldehydes, and epoxy-aldehydes can be interconverted to each other, and the reactivity of them all must be considered when considering the sensitization potential of the parent allylic alcohol. An in-depth study of the possible metabolites and autoxidation products of allylic alcohols is described, covering the formation, interconversion, reactivity, and sensitizing potential thereof, using a combination of in vivo, in vitro, in chemico, and in silico methods. This multimodal study, using the integration of diverse techniques to investigate the sensitization potential of a molecule, allows the identification of potential candidate(s) for the true culprit(s) in allergic responses to allylic alcohols. Overall, the sensitization potential of the investigated epoxyalcohols and unsaturated alcohols was found to derive from metabolic oxidation to the more potent aldehyde where possible. Where this is less likely, the compound remains weakly or nonsensitizing. Metabolic activation of a double bond to form a nonconjugated, nonterminal epoxide moiety is not enough to turn a nonsensitizing alcohol into a sensitizer, as such epoxides have low reactivity and low sensitizing potency. In addition, even an allylic 2,3-epoxide moiety is not necessarily a potent sensitizer, as shown for 2, where formation of the epoxide weakens the sensitization potential. /Geraniol/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Higher alcohols (>3 carbons) and related compounds/|/SRP:/ Basic Treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Higher alcohols (>3 carbons) and related compounds/|/SRP:/ Advanced Treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques, with a bag-valve-mask device, may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Monitor for signs of hypoglycemia (decreased LOC, tachycardia, pallor, dilated pupils, diaphoresis, and/or dextrose strip or glucometer readings below 50 mg) and administer 50% dextrose if necessary ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Higher alcohols (>3 carbons) and related compounds/

/HUMAN EXPOSURE STUDIES/ In a multicenter study, a total of 218 patients with proven sensitization to fragrance materials were patch tested with 5% nerol in petrolatum. The reactions were read at 2-3 days and in most cases, again at 2-5 days after the first reading. Positive reactions were produced in 6% of the patients (13/218).|/HUMAN EXPOSURE STUDIES/ A total of 314 patients were patch tested on the back, forearm and inside of the upper arm for 24-48 hr with 0.05-0.5% of nerol in either 99% ethanol (EtOH) or a base cream. Positive reactions were observed; (+) erythema in 2/314 and slight (+/-) erythema in 8/314.|/HUMAN EXPOSURE STUDIES/ A maximization test was carried out with 4% (2760 ug/sq cm) nerol in petrolatum on 25 healthy male volunteers. Nerol was applied under occlusion to the same site on the forearms of all subjects for five alternate-days 48-hour periods. Patch sites were pretreated for 24 hr with 5% aqueous sodium lauryl solution (SLS) under occlusion. Following a 10-day rest period, a challenge patch was applied to a fresh site for 48 hr under occlusion. Challenge test sites were pre-tested using 10% aqueous SLS under occlusion. The challenge sites were read at patch removal and 24 hr after patch removal. No sensitization reactions were observed.|/HUMAN EXPOSURE STUDIES/ In a pre-test for a human maximization study, no irritation was observed after a 48 hr closed patch test with 4% nerol in petrolatum on the backs of 5 healthy males.|For more Human Toxicity Excerpts (Complete) data for Nerol (10 total), please visit the HSDB record page.

geraniol

All other basic organic chemical manufacturing|2,6-Octadien-1-ol, 3,7-dimethyl-, (2Z)-: ACTIVE|Occurrence: Reported to be found in neroli oil (with geraniol) and in the essential oils of lemongrass, Ceylon citronella, ylang-ylang, champaca, cajenne bois-de-bois and bergamot, also in lemon, sweet orange, petitgrain bergamot, celery sage, lavandin, lavender, Mexican linaloe, myrrh, jasminem and Paraguay petitgrain. It has also been reported among the volatile constituents of curant aroma. Helichrysum augustifolium contains up to 30-50% nerol.

A mixture of [(2)H(7)]-geraniol, [(2)H(7)]-nerol, [(2)H(7)]-linalool and [(2)H(7)]-alpha-terpineol was prepared for use as internal standards in a rapid and accurate analytical method, employing gas chromatography-mass spectrometry (GC/MS), to determine the concentration of geraniol, nerol, linalool and alpha-terpineol in wine. The method avoids the possible formation, degradation and interconversion of these compounds during their analysis.

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Lipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]

Flavoring Agents