(2S)-6-methoxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid

• ChemBase ID: 158044
• Molecular Formular: C15H20O4
• Molecular Mass: 264.3169
• Monoisotopic Mass: 264.13615912
• SMILES: Cc1c(c(c(c2c1O[C@](CC2)(C)C(=O)O)C)OC)C
• Canonical SMILES: COc1c(C)c(C)c2c(c1C)CC[C@@](O2)(C)C(=O)O
• InChI: InChI=1S/C15H20O4/c1-8-9(2)13-11(10(3)12(8)18-5)6-7-15(4,19-13)14(16)17/h6-7H2,1-5H3,(H,16,17)/t15-/m0/s1
• InChIKey: MNBMVDGIDVXTOF-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-methoxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid
• IUPAC Traditional name: (2S)-6-methoxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-carboxylic acid
• Synonyms: (S)-6-Methoxy-2,5,7,8-tetramethylchromane-2-carboxylic acid; (S)-Trolox methyl ether; (S)-6-甲氧基-2,5,7,8-四甲基色满-2-羧酸; (S)-Trolox 甲醚

Database IDs

• CAS Number: 135806-59-6
• MDL Number: MFCD00171453
• Beilstein Number: 5481541
• PubChem SID: 162252180; 24889901
• PubChem CID: 688656

CALCULATED PROPERTIES

• Acid pKa: 3.827207
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.1294076
• LogD (pH = 7.4): 0.5556537
• Log P: 3.80533
• Molar Refractivity: 72.5618 cm^3
• Polarizability: 27.82177 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 143-145 °C
• Optical Rotation: [α]20/D -69±2°, c = 1% in ethanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0%; ≥98.0% (sum of enantiomers, HPLC)
• Grade: for chiral derivatization
• Optical Purity: enantiomeric ratio: ≥99.5:0.5 (HPLC)
• Empirical Formula (Hill Notation): C15H20O4
• Classification: Rare Derivatives of Natural Compounds

DETAILS

Sigma Aldrich - 93510

Other Notes
Chiral derivatizing agent for alcohols; some methyl substituted primary alcohols which are difficult to separate otherwise, can also be separated1,2