HHCB
Title: HHCB
CAS Registry Number: 1222-05-5
CAS Name: 1,3,4,5,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethylcyclopenta[g]-2-benzopyran
Additional Names: 6-oxa-1,1,2,3,3,8-hexamethyl-2,3,5,6,7,8-hexahydro-1H-benz[f]-indene
Trademarks: Galaxolide (Int. Flavors & Fragrances)
Molecular Formula: C18H26O
Molecular Weight: 258.40
Percent Composition: C 83.67%, H 10.14%, O 6.19%
Literature References: Isochroman musk odorant; scent is primarily due to the (-)-(4S,7R) and (-)-(4S,7S) isomers. Prepn: L. G. Heeringa, M. G. J. Beets, GB 991146; eidem, US 3360530 (1965, 1967 both to International Flavors & Fragrances). Prepn and olfactory characterization of enantiomers: G. Fráter et al., Helv. Chim. Acta 82, 1656 (1999). Synthesis of olfactorally active stereoisomers: A. Ciappa et al., Tetrahedron: Asymmetry 13, 2193 (2002). HPLC determn: W. Schüssler, L. Nitschke, Fresenius J. Anal. Chem. 361, 220 (1998). Subchronic toxicity study: A. M. Api, R. A. Ford, Toxicol. Lett. 111, 143 (1999).
Properties: Colorless crystals from methanol, mp 57-58°. bp0.8 129°. Strong musk odor. nD20 1.5342. d420 1.0054. Crystal density: 1.087 g/cm3.
Melting point: mp 57-58°
Boiling point: bp0.8 129°
Index of refraction: nD20 1.5342
Density: d420 1.0054
 
Derivative Type: (-)-(4S,7R)-Form
CAS Registry Number: 252332-95-9
Properties: Colorless crystals from methanol, mp 78-78.5°. [a]D24 -23.5°; [a]54624 -27.3° (c = 5.0 in ethanol). Powerful typical musk odor.
Melting point: mp 78-78.5°
Optical Rotation: [a]D24 -23.5°; [a]54624 -27.3° (c = 5.0 in ethanol)
 
Derivative Type: (-)-(4S,7S)-Form
CAS Registry Number: 172339-62-7
Properties: Colorless crystals from hexane, mp 57-58°. [a]D23 -25.1°; [a]54623 -29.2° (c = 5.0 in ethanol). Musky odor with dry aspects; slightly less powerful than (-)-(4S,7R)-form.
Melting point: mp 57-58°
Optical Rotation: [a]D23 -25.1°; [a]54623 -29.2° (c = 5.0 in ethanol)
 
Derivative Type: (+)-(4R,7S)-Form
CAS Registry Number: 172339-63-8
Properties: Colorless crystals from methanol, mp 77-78°. [a]D24 +24.1°; [a]54624 +28.0° (c = 5.2 in ethanol). Weak, musky, uncharacteristic odor.
Melting point: mp 77-78°
Optical Rotation: [a]D24 +24.1°; [a]54624 +28.0° (c = 5.2 in ethanol)
 
Derivative Type: (+)-(4R,7R)-Form
CAS Registry Number: 252332-96-0
Properties: Colorless crystals from hexane, mp 52-53°. [a]D23 +25.2°; [a]54623 +29.3° (c = 5.0 in ethanol). Very weak, mainly fruity odor.
Melting point: mp 52-53°
Optical Rotation: [a]D23 +25.2°; [a]54623 +29.3° (c = 5.0 in ethanol)
 
Use: Fragrance ingredient in perfumes, soaps, cosmetics, and detergents.

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