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| ADME/Pharmacokinetics |
Metabolism / Metabolites
α-Cedrol and caryophyllene oxide were incubated with Neurospora crassa, and the major metabolites were identified as 12β-hydroxycedrol, 10α-hydroxycedrol, 3β-hydroxycedrol, and 12β-hydroxycaryophyllene oxide. The antibacterial and free radical scavenging activities of these metabolites were evaluated in vitro using the broth microdilution method and autoradiography. However, no significant antibacterial and antioxidant activities were observed… Microbial transformation of (+)-cedrol was studied using Staphylococcus epidermidis, revealing that (+)-cedrol undergoes stereoselective hydroxylation at the C-3 position to generate (+)-(3S)-3-hydroxycedrol. |
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| Toxicity/Toxicokinetics |
Toxicity Summary
Identification and Uses: Cedarol forms colorless crystals. It is found in the wood of cypress and cedar trees, such as Atlantic cedar (Cedrus atlantica), European cypress (Cupressus sempervirens), and Virginia cypress (Juniperus virginiana). It is used in spices and as a flavoring ingredient in food and traditional medicine. Human Exposure and Toxicity: In one exposure study, researchers presented 26 healthy adult volunteers with air containing cedarol and blank air, respectively. Cedarol was continuously exposed at a constant concentration for 10 minutes, followed by 8 minutes of blank air exposure. Cedarol caused a relaxing effect, manifested as a decrease in heart rate, respiratory rate, systolic and diastolic blood pressure, and an increase in baroreflex activity. Parasympathetic activity was increased, while sympathetic activity was decreased. In another exposure study, researchers conducted a maximum dose test on 25 male volunteers using an 8% cedarol petrolatum solution. Two cases of anaphylactic reactions were observed in the 25 volunteers. In a preliminary human-maximized study, no irritant response was observed in five volunteers after 48 hours of closed-system administration of 8% cedrol. In another study, the antiproliferative activity of Pyrrosia lingua (PHVO) against human chondrosarcoma cells was evaluated. Twelve components of PHVO were identified. The major compound included cedrol (17.08%). PHVO exhibited potent antitumor activity against SW1353 cells, suggesting its potential use as a treatment for chondrosarcoma. In yet another study, the inhibitory effect of cedrol on the activity of eight major human cytochrome P-450 (CYP) enzymes was investigated to assess potential drug interactions. The study found that cedrol is a potent competitive inhibitor of CYP2B6-mediated bupropion hydroxylase with an inhibition constant (Ki) of 0.9 μM, comparable to the selective CYP2B6 inhibitor thiotepa (Ki value 2.9 μM). Cedrol also significantly inhibited CYP3A4-mediated midazolam hydroxylation at a Ki value of 3.4 μM, while β-cedrene showed weaker inhibitory activity against CYP3A4. 100 μM cedrol showed almost no inhibitory effect on the activities of CYP1A2, CYP2A6, and CYP2D6. Cedrol had a slight inhibitory effect on the activities of CYP2C8, CYP2C9, and CYP2C19, while β-cedrene did not. These in vitro results suggest that, given the potent inhibitory effect of cedrol on CYP2B6 and CYP3A4, its potential pharmacokinetic drug interactions should be investigated in vivo. Animal studies: A 28-day oral toxicity study was conducted to assess the toxicity of cedrol in rats. Sixty rats were randomly assigned to five groups (n=10 males or 10 females per group) and a control group of 10 rats. Twenty rats (ten males and ten females) were administered cedrol at a concentration of approximately 0.169% w/v, at a dose of 8.4 mg/kg/day, seven days a week, via gavage for 30 days. On day 28, one male rat was observed to have crooked incisors and oral swelling. Decreased absolute brain weight and brain-to-ovarian ratio were observed in female rats. However, these results were not consistent between sexes and lacked associated clinical changes, limiting the toxicological significance of these non-adverse reactions. An open-cut skin test with 8% cedrol was performed in non-inbred male and female guinea pigs, and no sensitization was observed. In another study on the sedative effect of cedrol, rats and mice were exposed to cedrol at a flow rate of 1.0 L/min for 30 minutes. The results showed a significant decrease in cumulative spontaneous kinetic activity in the cedrol-exposed group. Non-human toxicity values Rabbit skin LD50 > 5 g/kg |
| References |
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| Additional Infomation |
Cedrol is a cedrolane sesquiterpene compound, belonging to the tertiary alcohol class. It has been reported to be found in Mappianthus iodoides, Basella alba, and other organisms with relevant data.
Therapeutic Uses Cedrol, β-cedrolene, and thujone are bioactive sesquiterpenes found in cedarwood essential oil, possessing antibacterial, anti-inflammatory, antispasmodic, tonic, astringent, diuretic, sedative, insecticidal, and antifungal properties. These compounds have applications in traditional medicine and cosmetics worldwide. /Traditional Uses/ |
| Molecular Formula |
C15H26O
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| Molecular Weight |
222.372
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| Exact Mass |
222.198
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| CAS # |
77-53-2
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| PubChem CID |
65575
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| Appearance |
White to off-white solid powder
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
277.2±8.0 °C at 760 mmHg
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| Melting Point |
55-59 °C(lit.)
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| Flash Point |
115.5±10.9 °C
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
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| Index of Refraction |
1.519
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| LogP |
4.77
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
16
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| Complexity |
321
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| Defined Atom Stereocenter Count |
5
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| SMILES |
C[C@@H]1CC[C@@H]2[C@]13CC[C@@]([C@H](C3)C2(C)C)(C)O
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| InChi Key |
SVURIXNDRWRAFU-OGMFBOKVSA-N
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| InChi Code |
InChI=1S/C15H26O/c1-10-5-6-11-13(2,3)12-9-15(10,11)8-7-14(12,4)16/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14-,15+/m1/s1
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| Chemical Name |
(3R-(3alpha,3Abeta,6alpha,7beta,8aalpha))-octahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen-6-ol
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| Synonyms |
Eudesmol Cedrol AI3-02178
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~110 mg/mL (~494.67 mM)
H2O : < 0.1 mg/mL |
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.75 mg/mL (12.37 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.75 mg/mL (12.37 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.75 mg/mL (12.37 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.4970 mL | 22.4850 mL | 44.9701 mL | |
| 5 mM | 0.8994 mL | 4.4970 mL | 8.9940 mL | |
| 10 mM | 0.4497 mL | 2.2485 mL | 4.4970 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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