Articles:
3a(1H)-azulenol, 2,3,4,5,8,8a-hexahydro-6,8a-dimethyl-3-(1-methylethyl)-, (3R-(3a,3aa,8aa))-
Notes:
Constit. of Daucus carota (carrot)
Carotol was first isolated by scientists Asahina and Tsukamoto in 1925. It is one of the primary components found in carrot seed oil comprising approximately 40% of this essential oil. This sesquiterpene alcohol is thought to be formed in carrot seeds (Daucus carota L., Umbelliferae) during the vegetation period. Additionally, studies have shown that carotol may be involved in allelopathic interactions expressing activity as a antifungal, herbicidal and insecticidal agent.; It has been proposed that there is a direct cyclisation of farnesyl pyrophosphate (FPP) to the carotol (carotane backbone). This type of cyclisation is unconventional for the typical chemistry of sesquiterpenes. The only other proposed mechanism requires a complex ten-membered ring with a methyl migration. This later reaction, regardless of how plausible it may appear to be on paper, is energetically undesired and through the diligent work of M. Soucek and coworkers it was shown that the cyclization from FPP to carotol is the most probable biosynthesis route.
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| CAS Number: | 465-28-1 |  3D/inchi
|
| FDA UNII: | NT5C9M36DE | |
| XlogP3-AA: | 3.60 (est) | |
| Molecular Weight: | 222.37142000 | |
| Formula: | C15 H26 O | |
| NMR Predictor: | Predict (works with chrome or firefox) | |
Category: natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
| Google Scholar: | Search |
| Google Books: | Search |
| Google Scholar: with word "volatile" | Search |
| Google Scholar: with word "flavor" | Search |
| Google Scholar: with word "odor" | Search |
| Google Patents: | Search |
| US Patents: | Search |
| EU Patents: | Search |
| Pubchem Patents: | Search |
| PubMed: | Search |
| NCBI: | Search |
Physical Properties:
| Assay: | 95.00 to 100.00 % |
| Food Chemicals Codex Listed: | No |
| Specific Gravity: | 0.96460 @ 15.00 °C. |
| Refractive Index: | 1.49120 @ 15.00 °C. |
| Refractive Index: | 1.46300 @ 20.00 °C. |
| Boiling Point: | 109.00 °C. @ 1.50 mm Hg |
| Boiling Point: | 295.00 to 296.00 °C. @ 760.00 mm Hg |
| Vapor Pressure: | 0.000150 mmHg @ 25.00 °C. (est) |
| Flash Point: | 259.00 °F. TCC ( 126.11 °C. ) |
| logP (o/w): | 4.465 (est) |
| Soluble in: | |
| alcohol | |
| water, 8.507 mg/L @ 25 °C (est) | |
| Insoluble in: | |
| water | |
Organoleptic Properties:
| Odor Description: | pleasent mild |
| Odor and/or flavor descriptions from others (if found). | |
Cosmetic Information:
| None found |
Suppliers:
| BOC Sciences |
| For experimental / research use only. |
| (3R)-6,8a-dimethyl-3-propan-2-yl-1,2,3,4,5,8-hexahydroazulen-3a-ol |
Safety Information:
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| Not determined | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in Use Information:
| Category: | natural substances and extractives | ||
| Recommendation for carotol usage levels up to: | |||
| not for fragrance use. | |||
| Recommendation for carotol flavor usage levels up to: | |||
| not for flavor use. | |||
Safety References:
| EPI System: | View |
| AIDS Citations: | Search |
| Cancer Citations: | Search |
| Toxicology Citations: | Search |
| EPA ACToR: | Toxicology Data |
| EPA Substance Registry Services (SRS): | Registry |
| Laboratory Chemical Safety Summary : | 101679 |
| National Institute of Allergy and Infectious Diseases: | Data |
| (3R)-6,8a-dimethyl-3-propan-2-yl-1,2,3,4,5,8-hexahydroazulen-3a-ol | |
| Chemidplus: | 0000465281 |
References:
| (3R)-6,8a-dimethyl-3-propan-2-yl-1,2,3,4,5,8-hexahydroazulen-3a-ol | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 101679 |
| Pubchem (sid): | 135058678 |
| Pherobase: | View |
Other Information:
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| CHEBI: | View |
| KEGG (GenomeNet): | C09628 |
| HMDB (The Human Metabolome Database): | HMDB36579 |
| FooDB: | FDB015487 |
| Export Tariff Code: | 2936.21.0000 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
Potential Blenders and core components note
| None Found | ||
Potential Uses:
| None Found |
Occurrence (nature, food, other): note
| carrot Search Trop Picture | |
| carrot Search Trop Picture | |
| carrot root Search Trop Picture | |
| carrot seed Search Trop Picture | |
| carrot seed oil @ 5.68% Data GC Search Trop Picture | |
| carrot shoot Search Trop Picture | |
| carrot weed oil @ 9.85% Data GC Search Trop Picture | |
| parsley leaf oil @ 0.01% Data GC Search Trop Picture | |
| parsley leaf oil cuba @ 1.42% Data GC Search Trop Picture | |
| parsley plant Search Trop Picture |
Synonyms:
| 3aa(1H)- | azulenol, 2,3,4,5,8,8a-hexahydro-3a-isopropyl-6,8aa-dimethyl-, (+)- |
| 3a(1H)- | azulenol, 2,3,4,5,8,8a-hexahydro-6,8a-dimethyl-3-(1-methylethyl)-, (3R-(3a,3aa,8aa))- |
| (+)- | carotol |
| (3R)-6,8a- | dimethyl-3-propan-2-yl-1,2,3,4,5,8-hexahydroazulen-3a-ol |
| (+)-2,3,4,5,8,8a- | hexahydro-3alpha-isopropyl-6,8aalpha-dimethyl-3aalpha(1H)-azulenol |