484-68-4

Basic information

• Product Name: D-PINITOL
• Synonyms: PINITOL;3-O-METHYL-D-CHIRO-INOSITOL;chiro-Inositol, 3-O-methyl-;abietit;CUNEATE LESPEDZA EXTRACT
• CAS NO: 484-68-4
• Molecular Formula: C₇H₁₄O₆
• Molecular Weight: 194.18
• Mol File: 484-68-4.mol
• Article Data: 7

Chemical Properties

• Melting Point: 179-185 °C(lit.)
• Boiling Point: 317.2°Cat760mmHg
• Flash Point: 145.6°C
• Appearance: /
• Density: 1.56g/cm³
• PKA: 12.98±0.70(Predicted)
• CAS DataBase Reference: D-PINITOL(CAS DataBase Reference)
• NIST Chemistry Reference: D-PINITOL(484-68-4)
• EPA Substance Registry System: D-PINITOL(484-68-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 484-68-4(Hazardous Substances Data)

Usage

General Description

D-Pinitol, also known as 3-O-methyl-D-chiro-inositol, is a naturally occurring compound found in legumes, soybeans, and other plants. It is a type of sugar alcohol that has been shown to have various health benefits, including potential anti-diabetic, anti-inflammatory, and antioxidant properties. D-Pinitol has been the subject of scientific research for its role in improving insulin sensitivity and glucose metabolism, making it a potential therapeutic agent for managing diabetes and other metabolic disorders. Additionally, it may also have applications in sports nutrition and muscle recovery due to its ability to enhance glycogen synthesis and promote muscle cell hydration. Overall, D-Pinitol shows promise as a natural compound with potential health-promoting effects.

Upstream product

• 111015-73-7 DL-1,2-di-O-methyl-chiro-inositol 
• 124647-07-0 C₂₁H₂₂O₈ 
• 111392-29-1 (3aS,4S,4aS,7aS,8S,8aR)-4-Allyloxy-8-methoxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxole 
• 111392-09-7 (1S,2R,3S,4R,5R,6S)-3,4,6-Tris-allyloxy-5-benzyloxy-cyclohexane-1,2-diol 
• 98925-52-1 (+/-)-5,6-di-O-allyl-1,4-di-O-benzyl-myo-inositol 
• 58706-20-0 (+/-)-3,6-di-O-benzyl-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 98906-25-3 (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol 
• 98906-32-2 (±)-1,4-di-O-allyl-2,3:5,6-di-O-isopropylidene-myo-inositol 
• 51548-88-0 (+/-)-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 98906-30-0 (±)-2,3,6-tri-O-benzyl-myo-inositol 
• 80971-02-4 (1S,2S,3R,4S,5S,6R)-3,4,6-Tris-benzyloxy-5-methoxy-cyclohexane-1,2-diol 
• 87-89-8 D-myo-inositol 
• 77-78-1 dimethyl sulfate 
• 18311-26-7 methyl 6-O-trityl-α-D-glucopyranoside 

Downstream Products

• 14199-75-8 (1R,2S,3R,4R,5S,6S)-1-Methoxy-2,3,4,5,6-pentakis-trimethylsilanyloxy-cyclohexane 
• 54324-59-3 2,3,4,5,6-Penta-O-acetyl-1-O-methyl-myo-inositol 

Relevant articles and documents

Stereoselective oxidation of protected inositol derivatives catalyzed by inositol dehydrogenase from Bacillus subtilis

Inositol dehydrogenase (EC 1.1.1.18) from Bacillus subtilis is shown to have a nonpolar cavity adjacent to the active site, allowing racemic protected inositol derivatives such as 4-O-benzyl-myo-inositol to be recognized with very high apparent stereoselectivity.

An effective strategy for the synthesis of 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-phosphate related to putative insulin mimetics

Two glycosylinositol phosphates related to putative insulin mimetics, 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.

Mikrobial Oxidation in Synthesis: Preparation of (+)- and (-)-Pinitol from Benzene

Microbial oxidation with Pseudomonas putida of benzene affords cis-1,2-dihydroxycyclohexa-3,5-diene (2) which may be converted in five steps and 49percent overall yield to (+/-)-pinitol.Resolution of an intermediate alcohol (6) with menthoxyacetyl chloride provides optically pure materials which may be independently transformed to (+)- or (-)-pinitol.Demethylation conditions for pinitol together with further reactions of (2) and related compounds were investigated.