86918-62-9

Usage

Functional groups

Ketone, two hydroxyl groups

Appearance

Colorless to pale yellow liquid

Molecular weight

186.24 g/mol

Solubility

Soluble in water, ethanol, and other polar solvents

Melting point

Not applicable (liquid at room temperature)

Boiling point

Not available (decomposes before boiling)

Density

Not available (decomposes before boiling)

Sunless tanning products

Reacts with amino acids in the skin to produce a brown coloration, mimicking the natural tanning process.

Color additive

Used in the food and cosmetic industry for coloration.

Flavoring agent

Used in the food industry to enhance flavors.

Fragrance

Used in the cosmetic industry for scent enhancement.

Health effects

Limited information available; further research needed to understand potential health effects and long-term safety.

Environmental impact

Limited information available; further research needed to understand its impact on the environment.

InChI:InChI=1/C10H18O3/c1-2-3-4-5-9(12)8-10(13)6-7-11/h2-3,10-11,13H,4-8H2,1H3/b3-2+/t10-/m0/s1

Upstream product

• 25166-87-4 trans-4-hexenal 
• 1005326-90-8 (3E,8E)-1-hydroxydeca-3,8-dien-5-one 
• 225786-15-2 (S)-1-(tert-butyl)-1,1-dimethylsilyl (2-<2,2-dimethyl-1,3-dioxan-4-yl>ethyl) ether 
• 185553-83-7 (4'S,2R/S)-1-(2,2-dimethyl-1,3-dioxan-4-yl)hept-5-en-2-ol 
• 225786-18-5 (S)-2-(2,2-dimethyl-1,3-dioxan-4-yl)ethanal 
• 185553-79-1 (R)-2-<2,2-dimethyl-1,3-dioxan-4-yl>ethan-1-ol 
• 248582-05-0 (+)-(2S)-1-{2-[(E)-pent-3-enyl]-1,3-dithian-2-yl}-4-(trityloxy)butan-2-ol 
• 241819-10-3 2-(pent-trans-3-enyl)-[1,3]-dithiane 
• 248582-06-1 (+)-(2S)-4-{2-[(E)-pent-3-enyl]-1,3-dithian-2-yl}butane-1,3-diol 
• 225932-53-6 (S)-1-(2,2-dimethyl-1,3-dioxan-4-yl)-hept-5-en-2-one 

Downstream Products

• 51154-96-2 (R)-massoialactone 
• 61248-45-1 (6S)-6-pentyl-5,6-dihydro-2H-pyran-2-one 
• 248582-08-3 (+)-(3R,5Z,8E)-1,3-dihydroxydec-8-en-5-one O-benzyloxime 
• 248582-07-2 (+)-(3R,5E,8E)-1,3-dihydroxydec-8-en-5-one O-benzyloxime 

Relevant academic research and scientific papers

Asymmetric synthesis of (+)- and (-)-streptenol A

The asymmetric synthesis of (+)-streptenol A was carried out in ten steps and with high enantioselectivity (ee ≥ 96%). The key steps are the α- alkylation of 2,2-dimethyl-1,3-dioxan-5-one RAMP hydrazone A (1), subsequent deoxygenation and elaboration of the side chain via aldehyde B to furnish (+)-streptenol A in 23% overall yield. In analogy, the enantiomer (-)- streptenol A was synthesized using the corresponding SAMP hydrazone in 18% overall yield.

Enantioselective, organocatalytic oxy-Michael addition to γ/δ-hydroxy-α,β-enones: Boronate-amine complexes as chiral hydroxide synthons

An organocatalytic, enantioselective oxy-Michael addition to achiral γ- and δ-hydroxy-α,β-enones was developed. The key transformation is an unprecedented, asymmetric conjugate addition triggered by complexation between an in situ generated boronic acid hemiester and a chiral amine catalyst. Functionally, the intermediate amine-boronate complex acts as a chiral hydroxide surrogate or synthon. The resultant chiral β-hydroxy-ketones are obtained in good to excellent yields and high ee following mild oxidative removal of the cyclic boronate. Natural products (R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl acetate and (+)-(S)-streptenol A were synthesized to demonstrate the utility of this reaction. Copyright

Synthesis of (+)-(S)-streptenol A and biomimetic synthesis of (2R,4S)- and (2S,4S)-2-(pent-3-enyl)piperidin-4-ol

(+)-(S)-Streptenol A is synthesized by coupling a 1,3-dithiane with an optically pure epoxide. The absolute configuration of (+)-(S)-streptenol A is thereby correlated with that of (S)-malic acid. Stereoselective reduction of an oxime that could easily be