(Z)-3,7-dimethylocta-2,6-dienal structure

3D Mol Similar

(Z)-3,7-dimethylocta-2,6-dienal

: Iupac Name：(2Z)-3,7-dimethylocta-2,6-dienal; CAS No.: 106-26-3; Molecular Weight：152.23344; Modify Date.: 2022-11-25 07:22; Introduction: In the synthesis of vitamin A, ionone and methylionone. As a flavor and in perfumery for its citrus effect. View more+

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1. Names and Identifiers

: 1.1 Name; (Z)-3,7-dimethylocta-2,6-dienal; 1.2 Synonyms; (2Z)-3,7-Dimethyl-2,6-octadien-1-al(2Z)-3,7-Dimethyl-2,6-octadienal(2Z)-3,7-dimethylocta-2,6-dienal(Z)-3,7-Dimethyl-2,6-octadienal(Z)-Citral(Z)-Neral2,6-Octadienal, 3,7-dimethyl-, (2Z)-2,6-Octadienal, 3,7-dimethyl-, (Z)-2-cis-3,7-Dimethyl-2,6-octadienalBETA-CITRALcis-3,7-Dimethyl-2,6-octadienalcis-Citralcis-Citral=cis-3,7-Dimethyl-octa-2,6-dien-1-alcis-GeranialCitral bCITRALPQEXTRANeralneral,3,7-dimethyl-(Z)-2,6-octadienalNeroli aldehydeβ-Citral; View all

1.3 CAS No.: 106-26-3

1.4 CID: 643779

1.5 EINECS(EC#): 203-379-2

1.6 Molecular Formula: C10H16O (isomer)

1.7 Inchi: InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7-

1.8 InChIkey: WTEVQBCEXWBHNA-YFHOEESVSA-N

1.9 Canonical Smiles: CC(=CCCC(=CC=O)C)C

1.10 Isomers Smiles: CC(=CCC/C(=C\C=O)/C)C

2. Properties

2.1 Density: 0.856

2.1 Melting point: Melting point <-10 °C.

2.1 Boiling point: 229°Cat760mmHg

2.1 Refractive index: 1.456

2.1 Flash Point: 101.7°C

2.2 Precise Quality: 152.12000

2.2 PSA: 17.07000

2.2 logP: 2.87800

2.2 Solubility: 289mg/L(25 ºC)

2.3 VaporDensity: Relative vapor density (air = 1): 5.3

2.4 Autoignition Temperature: 225 °C

2.5 Color/Form: Mobile pale yellow liquid

2.6 Decomposition: When heated to decomposition it emits acrid smoke and irritating fumes.

2.7 Odor: Strong lemon odor

2.8 Odor Threshold: Aroma threshold values: Detection: 28 to 120 ppb; alpha-citral, 32 to 460 ppb; beta citral, 30 to 460 ppb.

2.9 PH: ACID VALUE: 5.0 MAX

2.10 Water Solubility: 289mg/L(25 oC)

2.11 Spectral Properties: Index of refraction = 1.4860-1.4900 at 20 deg C, not optically active

2.12 Stability: NOT STABLE TO ALKALIES AND STRONG ACIDS

3. Use and Manufacturing

3.1 Definition: ChEBI: An enal that is 3,7-dimethyloctanal with unsaturation at positions C-2 and C-6. It has been isolated form the essential oils of plant species like lemon. (Z)-3,7-dimethylocta-2,6-dienal Supplier

3.2 Usage: In the synthesis of vitamin A, ionone and methylionone. As a flavor and in perfumery for its citrus effect.

4. Safety and Handling

4.1 Exposure Standards and Regulations: Synthetic flavoring substances and adjuvants /for human comsumption/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Citral is included on this list.
Synthetic flavoring substances and adjuvants /for animal drugs, feeds, and related products/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Citral is included on this list.

4.2 Packing Group: III

4.2 Octanol/Water Partition Coefficient: log Kow = 3.45 (est)

4.3 Other Preventative Measures: If material not on fire and not involved in fire: Keep material out of water sources and sewers. Use water spray to knock-down vapors.
Personnel protection: Avoid breathing vapors. Keep upwind. Do not handle broken packages unless wearing appropriate personal protective equipment.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

4.4 Hazard Class: 8

4.4 Cleanup Methods: Environmental considerations- land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete.
Environmental considerations- water spill: Use natural barriers or oil spill control booms to Use natural deep water pockets, excavated lagoons, barriers to trap material at bottom. Remove trapped material with suction hoses.
Environmental considerations- air spill: Apply water spray or mist to knock down vapors.

4.5 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

4.6 RIDADR: 1760

4.6 Fire Fighting Procedures: If material on fire or involved in fire: Use foam, dry chemical, or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources.

4.7 FirePotential: Combustible

4.8 Formulations/Preparations: Citral has a strong, lemon-like, odor and a characteristic bittersweet taste. Commercially, the product is a mixture of two geometric isomers - alpha-citral and beta-citral, each exhibiting cis- and trans-isomers because of the position of the double bond. Geranial (trans-) and neral (cis-).
Citral from natural sources is a 2:1 mixture of two geometric isomers geranial and neral
Commercial material is a mixture of alpha and beta isomers.
Grade: Technical; pure; FCC

4.9 Protective Equipment and Clothing: Irritating to skin and may cause sensitization by skin contact. Avoid contact with skin and eyes. Wear suitable gloves.
Personnel protection: ... Wear positive pressure self-contained breathing apparatus.

4.10 Skin, Eye, and Respiratory Irritations: Irritant effect of 19 oils & 20 synthetic perfumes used in cosmetics were tested on skin of 50 male volunteers. Citral @ 32% concn was the most irritating of perfumes in human patch test.
Irritating to skin.
A cumulative irritation study was carried out on 8 volunteers. Patches were placed on the back daily, removed at 24 hr and read and them replaced with a fresh patch, over a period of 21 days. /Citral concentrations tested included 1, 4 and 8% in petrolatum./ The 8 % concentration was found to be a marginal irritant.
During an investigation of an outbreak of dermatitis following the introduction of a lemon-scented detergent, citral was shown by patch tests to be a strong primary irritant if applied in association with heat; 10% citral induced slight responses at 23 deg C and pronounced responses at 43 deg C. [Rothenborg HW et al; Contact Dermatitis 3 (1): 37 (1977)] PubMed Abstract

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Skin sensitization, Category 1

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H317 May cause an allergic skin reaction H319 Causes serious eye irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

7. Synthesis Route

106-26-3Total: 46 Synthesis Route

78-70-6 238 Suppliers

106-26-3 5 Suppliers

Literatures:
Montavon et al. Helvetica Chimica Acta, 1957 , vol. 40, p. 1250,1253
Yield: ~%

78-70-6 238 Suppliers

106-26-3 5 Suppliers

141-27-5 4 Suppliers

Literatures:
Porsch; Farnow Dragoco Ber., 1959 , vol. 6, p. 248,255
Yield: ~%

106-25-2 77 Suppliers

106-26-3 5 Suppliers

Literatures:
Kliman, Laura T.; Mlynarski, Scott N.; Ferris, Grace E.; Morken, James P. Angewandte Chemie - International Edition, 2012 , vol. 51, # 2 p. 521 - 524
Yield: ~99%

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8. Other Information

8.0 Definition: ChEBI: An enal that is 3,7-dimethyloctanal with unsaturation at positions C-2 and C-6. It has been isolated form the essential oils of plant species like lemon.

8.1 Uses: In the synthesis of vitamin A, ionone and methylionone. As a flavor and in perfumery for its citrus effect.

9. Computational chemical data

Molecular Weight: 152.23344g/mol
Molecular Formula: C₁₀H₁₆O
Compound Is Canonicalized: True
XLogP3-AA: 3
Exact Mass: 152.120115130
Monoisotopic Mass: 152.120115130
Complexity: 171
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 1
Topological Polar Surface Area: 17.1
Heavy Atom Count: 11
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceBwIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAAAAAADACggAICAAAAAACIAihSgAAAAAAgAAAACAAAAEgAAAIAAQAAAAAAgAAIAQIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10. Question & Answer

What is the chemical structure of the lemon flavor compound (Z)-3,7-dimethylocta-2,6-dienal? May 22 2023
Physical and chemical properties (Z)-3,7-dimethylocta-2,6-dienal is a chemical substance with the chemical formula C10H16O, molecular weight is 152.23, flash point is 101.7°C, boiling point is about 2..

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Price: 0.1 USD/kilogram
Time: 2023/06/28

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(Z)-3,7-Dimethyl-2,6-octadienal